How To Date Men In Your 30s, 40s, & Beyond

Are you in your 30s, 40s, or older and back in the dating game? Well, you’re not alone. My Guest, Christiana Cioffi, empowerment ambassador and author of the book “The Unapologetic Spinster, joins me to give listeners a guidebook for dating men later in life. She addresses the question “Is dating a numbers game?”, and shares her deal breakers, rules for dating, and how to deal with breadcrumbing, ghosting and more.

If you are looking for love, you’ll be well on your way to charting your course to your next big love by the end of this episode.

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Transcript

Speaker 1: 0:49

Do the sex Think fun, honest and feminist as fuck, and always with the goal of fighting the patriarchy. One female orgasm at a time. Welcome to the locker room. Today's locker room talk and shots topic is how to date men in your 30s, 40s and beyond, according to an unapologetic spinster Folks. I know firsthand the pains of dating later in life. I know how difficult it can be to get back into that world and find what you want, especially when you are a woman who is dating men still. Fortunately, though, there is no guidebook per se for us ladies. There are brave, brave women who have been willing to dive in to the dating pool, document their experiences and create a bit of a roadmap for the rest of us, if we are willing to listen. I, for one, am ready and willing to listen, and today my guest happens to be one of those women.

Speaker 1: 2:04

Her name is Christy Chaffee. She is a seasoned leader with a rich background in the United States Army and biotech industry. She is also an empowerment ambassador and a speaker who shares insights and inspiration, empowering women to unlock their authentic selves. I love that. Christy's dynamic journey started at the United States Military Academy at West Point, followed by five years serving as an officer in the US Army, with two years deployed in Iraq. She's also a decorated, very decorated officer. She is also, on top of all of that, a breast cancer survivor and the creative force behind An Unapologetic Spinster a dating blog and now a book that fearlessly explores modern dating. Christy, I'm excited to talk to you. Will you take a moment to tell my listeners a little bit more about you?

Speaker 2: 2:59

Well, thank you so much for having me. It's a pleasure to be here. I think you did a great intro on me. I don't know how much else to add other than say I've done a bunch of different things at 41 years old Now. I was in the army, then transitioned, got my MBA, went into the biotech industry where I rose up the ranks very quickly there. But now my passion and my work collide. Not no longer marketing, now it is all about empowering the next generation of leaders by unlocking their authentic selves, and I think that also ties to my book, which is about being unapologetic and how you date later in life.

Speaker 1: 3:37

I love it. So, listeners, I want you to listen all the way through. You are going to get lots of fantastic tips maybe some you've heard, maybe some you haven't from the experience she's had, and she'll be sharing that with us. I would also like you to head over to my YouTube channel, which is at Annette Benedetti that is the handle, because you can watch this over there. And the other thing that's wonderful is, if you have comments or questions about what you hear here, you can just drop it in the comments, which I get instantly and can respond to or get answers to for you right away. So stay to the end, because we are going to sum up this podcast with a little takeaway handbook for dating men later in life.

Speaker 1: 4:21

Anyways, I am ready to dive in. How about you? I'm ready. Let's go, all right. Well, let's get our drinks, cheers. Let's get ready to talk about dating later in life. I'm ready. I am ready. I'm ready for this conversation and to hear what you have to say. I read your book. Well, I want you to introduce your book and tell my listeners a little bit about it.

Speaker 2: 4:44

Well, my book is called An Unapologetic Spinster True Modern Dating Stories. I found myself single after a 10-year relationship that went from the age of 24 to 34. So when I'm 34, which is now about seven years ago I found out firsthand what modern dating is all about. It's no longer meet somebody you know in the grocery store and lock eyes and fall in love. It's swiping right and left until you get carpal tunnel syndrome. And I was living in Boston at the time and had so many different dating experiences. I realized I needed to change my perspective on what dating meant to me, because I was really having a heck of a time, and it started my blogging, which then turned into writing a book. And so the book is meant to be relatable, witty, humorous. 75% of it, I would say, is meant to be humorous, and then 25% is a little more heart-wrenching there. But it's all about the common experiences we have. Even though they're uniquely mine, they're very much shared with others that are out there trying to find love in this crazy modern world of dating.

Speaker 1: 5:53

Yeah, folks, it's a delightful book and it really resonated with me, even though I know that you and I are, incredibly, we're very different people for sure, different backgrounds, different interests but it was still as two women who are, you know, dating men, it was. So I had so many aha moments and moments of just not feeling alone, feeling less alone. You gave me that, thank you. I want to just dive right in and I want to start with an analogy you made that I thought was just lovely and insightful. Could you share a little bit about your analogy? Men are like avocados.

Speaker 2: 6:35

So first of all, this goes to the premise of it's a numbers game. I don't at all think dating is a numbers game, because I myself have been on a couple hundred first dates and that's what fed into these different stories that I wrote in my book. I actually think it's a. It is a timing game. So when you think about going to the grocery store and finding an avocado, because you're thinking about making guacamole or you know an avocado egg sandwich, whatever it is, you need an avocado for a specific time. So you go into the bin and you touch all the different avocados, seeing what's going to be ripe for when you think it's going to be ripe for when you take it home and want to make that guacamole. The problem is you touch a million avocados in the bin and maybe you find one. You take that avocado home, you put it on your counter. You're expecting to make guacamole in two days, but suddenly the avocado is ripe and you've got to stop everything you're doing and make your guacamole.

Speaker 2: 7:37

It's this timing that you can't predict and to me, men are avocados. They are not ready until all of a sudden, they are ready and, in my opinion, when they are ready, they turn around and they look for the first person that's picking them up, picking them up out of the bin, and that's the person that gets to take them home, and that's the person that's making guacamole with them. Doesn't have to be, you know, the home they really wanted to go to, but it's a, it's a timing game and it's kind of chance and, uh, it's. It's not a numbers game, is the ultimate premise that I'm trying to get at.

Speaker 1: 8:12

I agree with you 100%, and I want to just take one moment to talk to you about that, because I thought, I think to myself, you're right. The minute they decide they're ready, they turn around and they grab whatever woman happens to be standing there. That means basic criteria, right? They think she's hot, maybe get aroused or whatever. Oh, she's cute, she's funny, she seems laid back for a second and then they take her home, they hook a hookup with her and then cycle right back into how they ended up unhappy in a relationship in the first place.

Speaker 1: 8:45

And I guess that's one of my thoughts in dating that bothers me. It's like I don't want to be the one that just happens to be in the right place at the right time. I want to be the one that is. It's like oh, I see you and what you have is so special and so right for me that, regardless of where I am, I'm going to get my shit together so that we can be ready to do this thing. Do you think that that's just are my? Am I trying to be? Am I, too, idealizing things here? Is that a hopeless?

Speaker 2: 9:12

thought. I don't think that's hopeless because in some ways I think I'm the same as you. I don't want to be necessarily the reason somebody gets their shit together. I want that person to be ready for the kind of relationship that we're going to have, which is based off of trust and honesty and mutual growth. I don't need somebody who has all the same shared interests as me, but I do want somebody who's on a journey of growth.

Speaker 2: 9:36

So if that person isn't self-aware enough to know what they need to work on, as well as understand that I'm on my own journey and support me not as in push me, but like I want somebody who's on that journey with me. So they've got to come to a certain point of ripeness. If you will that, you know they can we can help each other the rest of the way. So I agree with you. I I think that there are people out there that are our. You know, the more ready we get, the more evolved we are on our journeys. Our standards are actually increasing, and I think that's a good thing because there are men. If we're into men, which I am, then there are men that are also on that journey of growth. I just haven't met them yet.

Speaker 1: 10:20

You're not the only one, no, but so I guess then what I'm saying is I don't want the kind of ripe. Maybe it's when they're ripe and about to turn rotten that they'll just take whoever is in front of them. I want the kind of ripe where it's like I'm ripe and I want something very specific. I'm not just going to take whoever is in front of me, because that just feels sad, like I don't want that kind of rape, ripe about to turn rotten is not for me.

Speaker 2: 10:49

I think that men who get ripe really fast and they don't even realize they've just gotten ripe. I think some of them find themselves in a physical relationship with somebody that I know. I know people in my life that are like I am not going to marry this person. But years have gone by and they are still with the person and or they've gotten married and so, against what they originally said, they found themselves almost trapped in this relationship and it's almost like they ripened while they were in it. But they were either too lazy to get out of it or they, you know, their their self-esteem, egos dropped. And I mean I was in a 10 year relationship that stopped serving me well before the 10 year mark came up and we we ended our relationship but I had lost my confidence. I had lost myself.

Speaker 2: 11:35

It was a codependent relationship, so not necessarily healthy. So when you look at a healthy relationship, people should feel fulfilled. But if they're not feeling fulfilled, there's probably some deeper issues there. So I think the ripening I am right there with you. I don't want to be somebody's happen chance that they ripen. No, I want them to be like it's me. It's me they've been waiting for, right.

Speaker 1: 11:57

Yeah, I do too. All right Cheers to that Cheers to that. Another little lesson in the book that I've talked about here on the podcast in the red flag zone. But I loved that you talked, in dating and dating men, a little bit about the breadcrumbs, what breadcrumbs lead to, and I love the story and I'd love for you to share it with my listeners. Let's talk about that.

Speaker 2: 12:23

I started that chapter writing about these two guys that I was interested in on the dating app. I spoiler alert never met them because one was Casper One. I called him Casper because he ghosted me and the other turned out to be a ghost as well because he was leaving me these breadcrumbs. So it's kind of like Hansel and Gretel and the breadcrumbs into the forest and you're following the breadcrumbs and then what happens? You're getting, you know, you know, poked by a witch with a stick or whatever you know it's. It is not a happy ending.

Speaker 2: 12:57

And for me, the breadcrumbs it was just enough. He was giving me, just enough to keep me interested on the app and not promising to meet me. Oh, we had to cancel this date. Oh well, let's reschedule it. And then what happens? He ultimately disappears. And so when somebody's breadcrumbing you, it's not straight ghosting, it's like walking me in to it and that's what breadcrumbing is. I'm, you know. It's not being direct, it's not treating somebody with a certain level of respect, because ultimately they just are going to go. You know they're going to disappear on you. So breadcrumbs lead to Casper who's ghosted you?

Speaker 1: 13:39

Yeah, so breadcrumbing is just giving you just just enough to keep you around until they decide whatever needs to be decided. And you know, I think, that the thing is with breadcrumbs you figure out, like, and they are figuring out, how hungry are you for the attention, how hungry are you for the love and the attention, and ultimately, whether it's from phone to trying to meet in real life or it's in real life in a relationship and trying to get to the next level, it seems to be that the breadcrumbs, if you are following them, usually lead to bad places or no place, but in well, hansel and Gretel's situation, they ended up in an oven.

Speaker 2: 14:22

Maybe not exactly let's hope not anything close to that. But also to your point, breadcrumbs can get smaller and smaller. How few breadcrumbs and how small can these breadcrumbs be? That you will still follow along. And this is in my story. I hadn't even met the guy yet. I hadn't even met him. And in my book and you know, and part of my dating philosophy was, I'm not spending a lot of time on an app because it's recreating the love at first sight in the grocery store and it was the vast majority of people you meet on an app, regardless of what their picture look like when you meet them, you're probably not going to be too attracted to a bunch of them, and that that chemistry, that organic chemistry, isn't there. So I hadn't. I was investing time following this guy's breadcrumbs and I hadn't even met him in person. What a waste of my time. And it was like you know what, if you're not ready to meet me, then Okay, but don't throw me breadcrumbs, no thank you.

Speaker 1: 15:14

I love the lesson of the breadcrumbs will get smaller and smaller so they can see just how little will keep you stringing along. It's such a terrible thing, by the way, it's a terrible thing to do to another human being to breadcrumb them like that. That's a terrible thing to do to someone else, but let's move on. So this is a good segue into after how many first dates did you say? You said you've gone on a couple hundred, you and I, both across my lifetime. But do you know exactly how many dates you've gone on?

Speaker 2: 15:50

I don't know. I know it is in a couple hundred. So I've been single for and I'm still single for seven years. I didn't go heavy on the dating apps for maybe for half of that time. I've been off the dating apps for two and a half years. At this point I'm never going back on. So now my dating is not. That volume is not there. But when I lived in Boston and even during COVID, I was dating and I you know I'm very competitive and I write about how I wanted seven dates in a row, seven days in a row, as a marathon of dating. It did not end well. I don't recommend it, but it is. You know it. To me it was. I thought it was a numbers game which pulls me back. It's not a numbers game, because if it was a numbers game, I know people that have met on the first date on an app and they got married. And how many have I been on and I've got my shit together. It's not. The problem is not me.

Speaker 1: 16:43

The problem is I haven't met the right person for me at the right time, right, but you did find the one and we will talk about that at the end. Folks, it's not like she is sad and alone and has cats. Do you have cats? That's the big thing.

Speaker 2: 16:59

So on my cover. You know I have my book right here. I've got my. My cat is on the cover with me. Unfortunately, I put my cat down in January. She's my best friend, had her for 15 years. She was 16 years old, so I do not have a cat. I have a dog now. He's a German shepherd mix and he's my buddy, but no cat.

Speaker 1: 17:16

So I brought up the number of people that you've dated because I want to allow listeners to take in the experience you are bringing to this conversation. Right, she has been on a lot of dates. So my next question is after going on hundreds of first dates, what are your deal breakers? What are deal breakers that are yours and that you feel should just be everybody's deal breakers?

Speaker 2: 17:41

I'll start with everybody's deal breakers. You should be, first of all, treating yourself with respect, and there's a lot to that. It's why I'm an empowerment ambassador, helping people build their confidence back up, because the love that we want to attract, we've got to start by giving ourselves and feeling that love and being that love, and that's how you're going to elevate the types of people you're dating and the experiences you're going to have. But, bottom line, people need to treat you with respect. They need to, they need to be respectful of who you are and, um, you know, and I think that's the bottom line. So if somebody is not respectful, if somebody you know there's so many different things people can do that are inappropriate on a date or before a date then you know you've got to take note of some of those red flags and move on from it. Even if you know you're very physically attracted to somebody or what have you, you've got to have appropriate boundaries and put yourself first.

Speaker 2: 18:33

So for me personally, deal breakers because I'm pretty fit, I'm very active, I want somebody who has similar interests to me in respect to that. So, um, no, smoking, I just I don't want to. I don't want to kiss somebody who smokes. I don't want to be around. That, it's just my personal preference. Um, uh, being physically active and working out, taking care of themselves.

Speaker 2: 18:56

Um, I'll give you an example. I'm a vegetarian, I was a strict vegan, pretty strict vegan for several years. But I don't care if they eat meat or not, right it's like. But they've got to be respectful of who I am. So if somebody is, like you know, is so convinced that I need to eat meat, you know there's a deal breaker. So it's it's an understanding of who I am and the journey I'm on and then being a part of that journey.

Speaker 2: 19:21

And then the last deal breaker is because I was in the army and I served in combat and I'm a fairly independent person. I'm also fairly petite, so I do have that kind of hardwired DNA drive to have somebody who's kind of a manly man, like an alpha male, if you will, which alpha to me is, you know, not a jerk, and alpha is just like a natural leader and we're confident. I want somebody who can cause I'm an alpha female match me Right and so be able to take care of me and physically protect me from harm if need be. And so those are some of my deal breakers that are personal to me, but at the end of the day, if they're not respectful and kind, if they don't, you know, if there's so many little things to that, then no, thank you, but you think that women should come up with their deal breakers before embarking on a dating life.

Speaker 2: 20:14

Yes, I think you also learn some of them as you go. Right, I think you've got to be open to your experiences and learning from them. So for me, what made dating okay and kind of a fun experience in general was I had three goals every time I went on a date. From the very beginning when I started, I had three goals every time I went on a date, from the very beginning when I started, I had three goals and there was a. The first goal was to learn something about myself through the process.

Speaker 2: 20:42

Somehow on that date, whether it lasts 15 minutes or two hours, I'm going to learn something new about myself as a result of putting myself out there and going out there. The second was learn something about something else. So it was you know, being, you know, more knowledgeable, usually about the career that they had, because I feel like I've dated every possible profession. So what their interests are, I would ask questions and I would try to find, you know, check that off by seeking something new. I was naturally paying attention to them and they were feeling valued in that conversation. And then the third was to go somewhere new. So I did not. When I started dating I was new to, fairly new to Boston, living in the South end, and I had not really been anywhere, and so I wanted to go on every date. I wanted to go somewhere new, and so I felt like I was getting something out of it. And through that whole process I grew, I changed and I realized more specifically of what I'm looking for and what I'm not looking for.

Speaker 1: 21:41

Well, I love that, so that, even if the dates did not end in a relationship or as someone you wanted to continue dating, you got something out of the process. You learned the city better, you learned something from the person you spent time with, so you didn't feel like, ah, I just wasted my time.

Speaker 2: 21:59

There were some dates where it was like you know that was a waste of time but the best I could do. I found to feel like it was a productive use of my time, resources, energy, mind, space, all of that. Dating is a big investment, especially on the apps and with the frequency that I was going I had to feel like there was something for me personally as a result of all of this.

Speaker 1: 22:22

And it definitely helped. I would like to move on to your dating rules. Can you share for listeners some of the rules that you have set for yourself, but that they, as maybe an empowerment coach, you would say here are some good rules for dating to set for yourself when dating men?

Speaker 2: 22:40

I have a rule about set a date. If you're on a dating app with somebody, set a date as quickly as possible. So if you're spending, you know, three weeks getting to know somebody and I put that in quotes getting to know somebody over a dating app, you're not getting to know them right. You think they're funny and then most of the time they turn out they're not funny or, you know, whatever the case may be, they're not who you think they are, because you're talking to them in an app, you're picking up tone and all of that, so you don't really know what you're getting. So set up a date as soon as possible. Um, and I had somebody say this to me once and I actually think it rings true If you don't set up a date within the first three days of connecting with somebody on an app, the chances of you lining up a date ever dramatically decrease. So if you're getting to five or six days that you've matched with somebody, I mean you can almost there's such a slim chance you're actually going to meet this person. Unless you are the type of person who has to text to get to know somebody and they are as well, then you guys are going to live in the dating app forever and then you're going to meet each other and you'll be like we have no chemistry. That was a waste of time. So it all comes back to line up a date in a safe environment as quickly as possible so that you can recreate that love at first sight in aisle seven of the grocery store. And it can be a 15 minute date. That's another rule. Make them quick. Don't go out to dinner. Don't look for a free dinner. Don't look to give somebody a free dinner. Just have coffee. Make it. You know coffee gets cold after 20, 30 minutes, right? If you're not done with your coffee, what are you doing? You meet you, you see whether or not you want to spend actual time together and you move on rather than have a drink which then somebody turns into. I'm going to grab some appetizers and before you know it it's been two hours and you already knew for an hour and 55 minutes you never wanted to see this person. So there's got to be some brevity in first dates and that helps you conserve your energy, your time and your money. And actually they will probably appreciate that as well, cause if it's a guy and they're paying for your drinks, like you know they're. They don't want to make it quick.

Speaker 2: 24:44

I say in in my dating, in my dating rules, that if somebody doesn't treat you with respect, you take them, kick them out to the trash and watch as the trash picks them up on garbage day, like you don't need somebody in your life that, from the very beginning of getting to know you, doesn't treat you well, and you'll see those red flags. Another one I would say is don't sext. If you are looking for love in a committed relationship, then sexting with somebody before you're in a serious relationship with them, or dating them or sleeping with them, it's just gonna make it a little more casual. It's going to naturally lend it to being casual. So let that naturally evolve. Get to know them, look for the emotional connection with somebody before you just jump into sexting with them because you don't even you don't even know them yet, right? So? And it's a digital footprint, you got to be careful of that stuff.

Speaker 2: 25:37

Oh, if he cancels a date, if he cancels a date and he doesn't tell you why and he doesn't reschedule it, move on. Move on immediately. He is not going to reschedule it, he's. It's not there. He either had another date. Pop up that he's more interested in or he's just flaky, so I'll move on from that. Also, you can tell in somebody's photos often if they are married or if you know so. If somebody is wearing sunglasses and has grainy photos, they're probably married. If you have no clean shots of them, they're married. Swipe left.

Speaker 1: 27:09

Oh, that's good insight.

Speaker 2: 27:13

I guess I didn't even think about like how you could tell if they were married or not. That's what I learned from personal experience. Went on a specific date with a guy and I was like, oh, I even said that to him. That's why all of your photos have sunglasses and they're very grainy. I was like, yes, it is. So I did not go on a second date with him.

Speaker 1: 27:28

Well, now you know how to figure out if a guy is married. I'm pulling one over. How awful, how awful. The other thing that you mentioned in your book that I want to talk about is you categorize men, the categories of men. Can you tell me a little bit about this concept, and then what the categories are and what they mean?

Speaker 2: 27:48

So this is how my mind works, and I came up with these categories as a result of people saying Christy, why haven't you met your person? Or why don't you just keep dating this person that you're seeing and you'll fall in love with them? They could be the one I said no, they're not. I already know that, like I know soon after I meet somebody, if I, if it's ever going to evolve into something, and so my challenge to the readers, and even to my friends that I talked to about this, is try to pay attention to what it is. You're almost feeling on an energetic level, and so people believe in soulmates or any of that energetic level, and so people believe in soulmates or any of that. Then you'll almost sense if somebody is that level of connection for you, but often, oftentimes, they are not. They could be a soulmate that's there to help you on your journey, but maybe you're never going to fall madly in love with them. You could date them for a period of time. So I have three categories, and it starts um a, b and C. So we'll start with C category. See, there's actually fourth one, which is the no zone. It's like when you go on a date with somebody and you can't remember their name two days later. Right, you've moved on. You did not. They were not remarkable, so they just go into a no zone category of okay, you tried it, move on. The C category would be those that are like the friend zone, if you will. So this is you know somebody that, um, you know you enjoy their company, but maybe you don't have the chemistry with them, maybe you don't see it ever evolving into anything and but you like them and you have shared interests. Maybe you'll, you know, go hang out, go golfing together or something who knows. So you got to kind of say like, do you ever want to see this person and is it more of a friend you also then, at B is the bangable. So this is where, okay, you know what, you've got chemistry with somebody and you know that maybe that for X, y, z reasons, or they have a deal breaker, but you still feel that chemistry with them and you want to date them casually. Well then, there you go. They're probably in category B.

Speaker 2: 29:43

Category B often does not go into category A, which I'll describe in a second Category B, if anything goes into category C or the no zone over time, which means that you'll probably have some casual experiences with them for a period of time. It'll evolve into either friendship or it'll just kind of fade away altogether. And then category A, that's your soulmate, that's like your person, that's what most of us are looking to find, this meaningful, emotional, spiritual, intellectual connection with somebody. And that is, so you know, so rare, but it's something that we're we're striving for. Some lucky people find it when they're young and others of us are, you know, later in life, still trying to find that connection and hold onto it.

Speaker 2: 30:36

Right so I've had several people in category a, but yet I'm not with them, right so, and I would even say my 10 year relationship was a category a, he was a soulmate, but it wasn't meant to last. So in each of those categories I go into a little bit of you know how to engage with them and how to you know how to. Category A, for example, is, especially if you're a woman dating a man, you want to have that emotional, you want to make sure they have that emotional connection with you before you just sleep together, because that's a quick way to get them to kind of not get there emotionally.

Speaker 1: 31:11

So as you're dating, you can categorize the guys and kind of know where it's likely to go. So I'm going to assume by this method you are okay with or that you support which seems to make sense to me dating multiple people until you kind of one rises to the surface and you focus in yes.

Speaker 2: 31:39

Men are dating multiple women. What is? If you are not in a committed relationship with somebody, then why are you exclusive with them? And just because you're dating somebody doesn't mean you're sleeping with them. So, and it's all you know, everybody's got to be safe and do what's right with their values and you know their interests. But, yes, I would say, don't put all your eggs in one basket, because that's a quick way to put a lot of pressure on a situation and then you're now focused on them energetically and you're thinking about them all the time and they're they're dating multiple people too. You should be out there dating multiple people until somebody really catches your eye and then, when they've caught your eye and you're really interested in them, still don't put all your eggs in one basket, because that you want to allow them the breath, the room to breathe, to catch up to where you are, and that's you know. So don't be in a committed relationship before you're in a committed relationship.

Speaker 1: 32:37

Don't be in a committed relationship before you're in a committed relationship. I wonderful advice because I think oftentimes women especially mostly women and because of our conditioning, we go out on a date with a guy. It goes well, we get a little spark and then we're just like I'm not going to date anyone else because then he'll think X, y, z about me and I'm just like, if he's the kind of guy that would do that, you don't want to date him anyways. Perfect advice.

Speaker 2: 33:05

So when you start dating, you're going to be dating multiple people and categorizing them yes, he's dating multiple people and if he's not having that conversation with you about, hey, I really like you and, fairly early on, I would like it to see where it can go between us and you're feeling that and it's mutual and okay, yeah, like, let's, let's press pause on our dating labs, let's press pause and dating other people and see where this goes. It doesn't you know, it doesn't it? Maybe it just alleviates the pressure. Whatever you got to be direct, honest and open with the person that you're dating, but they need to be that way with you, you too. But don't jump the gun if somebody hasn't emotionally gotten to where you are.

Speaker 1: 33:50

Right. So what you're saying is that becomes a mutual decision where you're both like, hey, we're at this point where we both really dig each other and have these feelings, it's time to pause the other, and you both agree to that. It's a like said and known thing.

Speaker 2: 34:07

Yes, but let's also talk about what a lot of my single girlfriends do. They're on some of these apps and they can see when the guy that they're dating that they're not in an exclusive relationship with when he's active or what he's doing, and they're constantly wondering what's he doing. So they're getting on their app to see if he's been active or whatever, and it's like stop doing that. Stop doing that, because that is just not healthy for you. You're worrying more about the other person than you are about yourself and your own needs, and if it's meant to be, then it will happen. It will happen.

Speaker 1: 34:37

I love that you say that I do feel like it's so reassuring to hear from you also this belief that when it's meant to happen it will, because if somebody really sees you and sees in you something that is valuable and that they want and that they love, then regardless of where they are I'm going to say, in their ripeness or in life they are going to find their way to you and to be with you. You know, that is what happens when you meet someone who sees you and values your worth and is like I want to be in this person's life. I'm going to make it happen, even if it's a challenge, because I know that's what I do when I feel that way about somebody and I'm looking for someone to match me my energy, my dedication and how I feel about relationships. So that's a wonderful piece of advice. I want to move on to you tell a little story about kissing and the importance of kissing.

Speaker 1: 35:42

I just thought it was fun. I do strongly believe in kissing compatibility. I want to know two things, because in the story and you can relay it if you want, like you definitely were like hey, if the kissing isn't working, it's not working. I'm going to let you tell that story. But I have two questions that I think are important for women looking for advice in dating men A. For women looking for advice in dating men A how long do you think you should wait for the first kiss? And B we're going to follow that up with how long do you wait to get to banging?

Speaker 2: 36:16

Okay. So let's start with how long should you wait to kiss somebody? Yeah, kiss somebody, yeah. The simple answer to that is as long as you want to wait. I mean, I. I don't think there's a right answer to that. I think it is.

Speaker 2: 36:36

Everybody is individual and some people are like I don't kiss on the first date, okay, don't kiss on the first date. It's to me, it's a, it's a kiss and it's you know, I'm 41, I'm 41. What am I like? I'm getting. I'm not getting younger, I'm not 18 years old, I'm not, you know, meeting somebody in a bar when I'm, you know, I've been drinking. Like I'm on a date with somebody with the purpose of finding love. And if I feel a connection with somebody and for me that is emotional, physical, intellectual, and I think they're feeling it too then chances are, by the end of the date there's going to be a kiss. So I there's. That to me is great, because to me and I think that's what my story is about is how does somebody kiss? Because we're not, we all don't kiss the same and we all have certain preferences or ways that we want to be kissed and whatever, certain moods or what, what have you? But, um, yeah, I write about how somebody was checking all these boxes and it was like waiting was waiting and waiting for the first kiss and when I finally got it it was such a letdown I was like I wish this had happened on date one Cause I wouldn't have gone on two more dates with him waiting for this first kiss. So to each their own on their timing, but for me I, if I know, I know, very quickly into a date, if I, if I think there's potential, and then it's just a matter of you know, and sometimes I really like somebody, but I don't want to date, I don't want to kiss them on the first date. It all depends, but I don't think there's anything wrong with kissing somebody on the first date.

Speaker 2: 38:09

Second question of how long do you wait to sleep with them? Well, it depends on what you want, and I think that's where the categories come in, because if you are looking for your soulmate category A and you really want, you're hoping that this person that's sitting in front of you on this date is that you're feeling a lot and you're like this this is somebody I've been waiting to meet, like I want to see where this goes Then I strongly advise you don't sleep with them. I strongly advise you allow them, especially for men, because they are, you know, more visual and it's going to take them time sometimes to like you and develop those feelings or be open and accept their feelings. I think you just let that evolve and you see where it goes.

Speaker 2: 39:44

I would highly recommend wait till you're in a committed relationship or exclusive, exclusive relationship with somebody that you want in category a before you sleep together, because otherwise I think it just gets messy and that's my experience and I don't recommend that. So if that is, you know, if you fall madly in love and you have a marathon date that goes all day you meet it for coffee in the morning and you're hanging out at the end of the day, you know you're probably still a lot of emotions and hormones happening there I'd still wait. I would not jump into it. If that's somebody you really want to see things work, but if it's more casual, then you know it's. Again, it's similar to kissing. It's what is what's going to work for you based off your values.

Speaker 1: 40:29

But then what if you wait and wait and then fall in love and then you have sex and you're like, oh, oh, you're not like it's bad, it's real bad.

Speaker 2: 40:40

Is it salvageable bad or is it just like really bad?

Speaker 1: 40:44

I mean, that's always the question. That's always the question isn't it.

Speaker 2: 40:47

I feel like you have an idea of whether somebody is going to be good in bed or not based on how they kiss. So that's to me another reason of like why and yeah, so I, I there's nothing wrong with doing, you know, having some fun like a teenager for a little bit maybe.

Speaker 1: 41:04

But like I would dry humping is okay, you can dry hump maybe get a little first base, second base action, before you go for the hardcore commitment. I like it, I like it.

Speaker 2: 41:17

I mean you could right. I just think that if you also have fallen in love with somebody, then chances are it's probably not that bad. Quite frankly, it's probably not that bad, because if they're in love with you too and you have an emotional connection, then there's there's more um, you know, there there's there's energy, positive energy, being exchanged between you as you're you know doing that, and um also, if somebody is, you can help somebody along, like hey, I would really like to be kissed this way or this or that, like you can share what your preferences are. It's part of being an adult is saying this is what I like or this is what I don't like. And if you can't communicate that, then maybe you're not where you think you are, in that you know connection with the person.

Speaker 1: 42:11

Right, right. Well, I always say you shouldn't be having sex if you can't talk about sex with the person you're with. I'd like to know why you got off the apps and why you're choosing not to go forward with apps.

Speaker 2: 42:22

I think the reason is the same because it was not a good investment for me, for my time, money, energy. I found that I was coming up empty handed and that my person I do not believe that my person I was going to meet on a dating app. Anybody I felt a real connection with I met in the real world and I talk about those experiences in my book, like on a running race, because I run a lot on a scuba trip introduced by friends, what have you. It was never in a dating app. The last date from a dating app that I went on was probably the best connection out of everybody on the dating apps that I'd been on, but it didn't work out and for stupid reasons, mostly on his part, and that's where I'm like I'm done with dating apps. If this was the best I got out of X number of years and hundreds of first dates, I'm done.

Speaker 2: 43:14

This is not how I meet my person and I give it up to the universe and that's also part of my stories. I'm right where I'm meant to be. So you know, sometimes you just got to let good things come to you and that's and when. And to do that you've really got to believe that you deserve it and that it will come to you when the time is right, and that's where I'm at. So I don't need to go on a dating app, because I don't need to force this to happen. I'm going to meet the person that I could meet on a dating app. That's the person. I'm going to meet him. I can meet him in the grocery store for real, and that's that's where I leave it. That's my belief system, and it has saved me a lot of time, money, energy that I've invested into myself and other things that I want to do to make myself happy in this life.

Speaker 1: 44:02

Right. This is so resonant with me because I definitely apps are not in my now or ever again, and also with the not investing all that time into seeking this other person. I have been able to like, in a very short period of time, accomplish amazing things, which is great. But so the moral of the story is you found the one correct. You found the one while dating, and the one was yourself.

Speaker 2: 44:39

Yes, and that is I start the book off this way and I end it. The love we all so desperately seek is already within us. And that came to me as I'm big into meditation, as I've been going on this journey of, you know, kind of reinventing myself, if you will, after my 10 year relationship and trying to understand why was I having, you know, dating unavailable men or having these certain experiences. It's like, well, let's pause and put the focus back on me. And you know I went.

Speaker 2: 45:07

You mentioned in the beginning I'm a breast cancer survivor. I was single going through that and I had to hold my own hand through that. I've moved across the country, I've done, I built a house. You know I've done all this stuff on my own and I'm very proud of my ability to do that on my own.

Speaker 2: 45:23

So when I meet the person I'm going to be with, I'm going to have such great respect for the role that they play in my life and I'm going I, you know I say this I'm not going to take them for. For you know, I'm not going to take them for granted. And I think a lot of people do that because they forget that this person isn't there to make them happy. You're here to your job is to make yourself happy. You can't put that onto somebody else. So I will have a different view of what a committed relationship and what my person for the long term is going to, what role they're going to fill in my life. And that is not one of filling a gap, that's one of being you know on a journey, that I can support them on their journey and we can experience things together. But that's not possible if you don't realize that the love of your life is you.

Speaker 1: 46:16

I agree. I agree with you 100%. So there you go. I want to have you leave my listeners, women in their 30s, 40s, 50s right now, who are jumping into dating or ready to find a person or hoping to find, and I'm going to obviously your expertise. I did not ask, but it's you are heterosexual, correct? Yes, I am Okay, because your expertise is dating men and your experience and the advice you've given and shared. What is your top piece of advice for a woman in her 30s, 40s, 50s and beyond wanting to start dating, wanting to find a man? What is your top piece of advice for?

Speaker 2: 47:02

them. It is never too late to find love, and if you think it's too late, then you're not enjoying the moment of where you are in your life and all the things you have to be grateful for. So stop obsessing about the future and, when things happen, and enjoy the now, because that person will come when the time is right.

Speaker 1: 47:25

That person will come when the time is right. That is my mantra. So thank you so much. This has been a really fun, enlightening talk. I want you to tell my listeners where to get your book. It is truly delightful. I for women who are dating right now, or even if you're not, you've dated in the past, but especially those who are later in life dating, it is a delight. I really enjoyed it. Lots of relatable information. You will feel less alone and I think by the end of the journey, of reading about your journey, you also feel hope and maybe have some insight on how to redirect your own energy and hopes and dreams. So can you please tell everyone where to find you?

Speaker 2: 48:14

So my book is An Unapologetic Spinster True Modern Dating Stories by Christiana Chaffee. Christiana is my full name and you can find it on Amazon. Got a bunch of great reviews. If you're still on the fence, read, check some of them out. I have a website for my book. It's called unapologeticspinstercom, but actually my primary website is christianachoffeecom, and that's where you can also learn about me as an empowerment ambassador. You can see some of the things that I'm doing, as well as a link to my book further details there. So you can find me on LinkedIn as well as the other major platform I'm on.

Speaker 1: 48:49

Wonderful. Thank you so much for joining me and for this conversation. Ladies out there dating guys. Godspeed Cheers. Thank you so much for having me. Yes, thank you for being here and, to my listeners, until next time, I'll see you in the locker room. Cheers.