Dear J.D., Signed Hopelessly Single

Hey, it's Louise of I do part two jumping back into the conversation with single guy JD. So, in the world of dating, right, it is hard to know when you're navigating a person that you're just talking to and you don't know their baggage and they don't know yours, right, So we're all just kind of coming with our own kind of cloudy lens.

Right.

So I find that there are some people that are super kind of transparent. They came, they saw, they conquered, right, They're just super direct.

And then I find that.

There's people out there that will you know, you know, I would say not for our age, but basically a version of sliding into our DM, right, that would be for our kids age, But that version of like somebody who's making the outreach and like dipping their toe in and then doing the back and forth, and then they like they like ghost you and they go quiet when you weren't the one who reached out anyways.

Does that make sense?

Like, I don't know if that's a.

Function of these people are just you know, kind of throwing a lot of balls against the wall and seeing what sticks, or they are just you know, kind of insecure you know people or it's interesting to see that. And I hear a lot with friends of mine when they go on kates with guys, and it's interesting to me, And I would love to know, like what you think about why there are people that literally make, you know, outreach and then literally don't do anything with it.

Yeah, I think that's a I think it's a little bit of a function of our time in the sense that you can contact so many people so quickly that it does allow people whether you're on DMS or Instagram or whether you're on you know, bumble or match or something, you have the ability to contact a lot of people and reach out to a lot of people, right, And so I think and sometimes people like they'll get a response from somebody and that was the person who was

And so there's some of that.

They got lucky that the person that was at the top of their list responded and then they just stop chasing others. But so that that I think is a functions on other I think people are also just maybe just looking for attention and flirting where they're not as interested.

As they they let on. Right, they enjoy the.

Flirtation, the game, They enjoyed the game.

They enjoy the game, They enjoy the flirtation, but when it comes down to it, they don't have the energy or the time or the interest in chasing two or three women at once, and so they flirt with ten women, but they only really pursue one or two because they run out of time, and so they're but they're flirting with ten and pursuing two.

It's a weird, but that can happen. Right.

Well, it's interesting because you know, there've been so and I don't I don't do dating apps, but there's been so many articles lately that people are you know, kind of you know, basically moving off of the dating apps because it's almost like thirty one flavors. Right, You go on a date, you come home, you're like, yeah, it was fun, but the next person could be better, So you just keep swiping, swiping, swiping, so you're never, never satisfied with what's in front of you.

So it feels like people are you know, trying to make more.

Of a concerted effort to do old school meetups or you know, join a running club or hire a matchmaker, or a little more point and shoot. So you're hearing like, you know, like bumbles letting or hinges letting go of you know, employees or whatever.

So I think that would would be great.

Like I just think the numbers game is just it's too It's like a sensory overload.

Yeah, I agree. I was well. Two things.

One is I was talking to a a guy friend of mine who there was a service that women pay for, like for them to get introduced two men, and so they like curate dates with men for these women. This is like a high end, high price whatever thing. But so I think people are looking for a more point

In an app?

The amount of time she was just saying, the amount of time it takes I got to go on ten dates to get to one person who I'm both interested that I'm interested in their looks because that doesn't act as a picture, or that I that I that the conversation was good right in person, not the text conversation, which doesn't always reflect how somebody's vibe really is in person.

They can be much better on texts, especially right right.

Right, And so so I was trying to convince to you, like you're you're what you can accomplish in two hours in a restaurant or a bar a happy hour is what's taking you two or.

Three weeks in the apps?

Right, So, like I was exactly advocating for that, like that old school where you go to two or three restaurants and you're around seventy five people who live in your town and are single, and you get to talk to two or three in person is actually in some ways better and faster than this longer drawn out You text for three weeks, you meet one person, you do that again, and now you've met ten people in ten weeks versus ten people in one weekend.

Right, So, anyway, I'd like to see some of the old school stuff coming back for people.

What do you think about the concept of recycling?

Right?

So I love to do this, right. One woman's trash is another woman's treasure.

Right So just because there was no kind of connection or love spark between me and something doesn't mean that there might be something between somebody else. So I'm always one who loves to do that, and I think women are very open to that. Are men open to that? Like, have you ever gone out with somebody that you're like, she's great, but she's not right for me. I think she's a better fit for this person.

Yeah.

Well, first of all, I agree with you.

I'm a big fan of that idea because you've got to know the person enough to know they don't fit for you, but you also had a light bulb go off that they fit this other person that you know.

I think it's fantastic.

I think it's a compliment.

It's like I liked you enough not for me that I want to introduce you to somebody who means something to me.

Yeah, I think it's a compliment, and if people take it the other way, then they're two sensitive. But I would say for the guys, I would say it needs to be early on, right, if you dated the if you went on one date with the person, it's great. If you went on if you dated for a month or two, they're less likely to man can get weird about that piece, right, Like now I'm dating your ex girlfriend I'm talking about.

Yeah, oh yeah, yeah.

I had been dating this guy for like.

Six months or seven months and we broke up, and so my friend said, well, why don't you set him up with so?

And so I go, no, he's an ex boyfriend, like boyfriend, that's like not happening.

Like you know what I'm saying, Like, and I don't know if that was a function. I just want to make sure I was, you know, I don't know what it was, but something about that just did not feel it.

Yeah, two dates is great, but yeah, when you get into the months, it's a little less fun to hand it off. I've actually gone and asked friends of mine about girls they dated for three to six months, like would you be okay if I asked her out?

And some of them said yes, and some of them said no.

Right, that probably has to do with who ended it right and if it's resolved or not resolved.

Well exactly, So, yeah, you got to make the handoff quickly.

Yes you do, okay, So let's move on to a question from Teresa.

So Teresa is asking a question about is it important for you to have a sense of her body count the number of guys that she slept with. So I would assume Teresa has probably slept with a lot of people, which is why she's asking this question.

So is that a topic that you want to have a conversation about or is it weird? Is it invasive?

Yeah? I don't.

I've never asked a woman that in my entire life. I've had women offer it up to me and share it during because they were actually sharing it so they could ask me about mind. So they were doing it as a lead in, which was fine. But unless a woman led me into that conversation, I'm not going to ask a woman that. I think you you get to know somebody you get a sense.

If they are.

I don't know, are you going to get a sense organically whether it's four or forty, If it's four hundred or four thousand, you'll probably start to figure that out from I don't know her friends or or her you know her her social media, but I don't. I think it's a personal thing, and I don't think it's super relevant to whether the two of you are connecting or not. And if it's a real big outlier where it's one person or it's five thousand, you're going to sense that anyway.

Ability to read people.

But for most people it's in a normal range and it's all fine, and it's all going to work out.

You don't have to get into numbers.

I mean that's my view, right, So two responses to that.

So and again we all navigate in our own way, right. So for me, you know, I only.

I'm only sleeping with one person at one time, and if I'm only sleeping with that, we're totally exclusive, right, So then I take it a step further, which is really interesting, And I've never gotten pushed back on this, right, but I actually make a guy get an STD test period and I've never.

Gotten pushed back. And so for me, I have a boundary that's super super clear.

And you know, I have other friends who you know, they'll you know, do whatever all the time, no condoms, whatever, Right, So I just am terrified of getting something, you know what I'm saying. And so, and I also want to know that if I'm going to I want it to just be with us and I'm in it. What happens when you just start dating somebody and they're just out of their divorce and you learn that the only person she has ever slept with in her entire life is

Yeah, I mean.

It is definitely something to ponder for a minute, in the sense that if you're not interested in her, if well, let me say this, first of all, there's unless she met the person and married them at twenty one.

There's a good chance that she dated people before him, But let's say she didn't.

The first boyfriend she's ever had and the only person she's ever been with is her husband.

I would say, I would say, if you're.

Interested as a guy, the chances are you're actually I don't think it's intimidating as much as you're likely going to get that much of a better like instead of being stressed about it, you're actually more likely to get compliments because she's had this bad thing for so long that has been dragging out for so long that that it's just going to make you look good as a guy.

And also obviously it means something to her that she's just not throwing a cat at all the time. So if she's willing to take that step with you, it's almost validation too that she really likes you.

Right.

Yeah, one is she takes her relationship seriously. She hasn't stupp with a lot of people, so yeah, that just shows she's interesting, which is a compliment. And there's no reason to be intimidated as a guy like in that, why are you, like, why would you be intimidated by it?

But I do think it's a compliment.

So uh, and I have since might worst dated people who kind of fall into your category, and it was I thought it was a compliment. I didn't find it stressful, but I could see how someone might have to think.

About it for a minute.

Well, the best is when they'll call me and they'll be like, guess where I was today, and they're sending me a picture of their arm with like a blood test you know what I'm saying, like getting their sc tests as in. And I'm like, they're like right on it, you know what I'm saying. So so then we kind of have Yeah, that's good.

Look, it's it's that you're you're letting them know that like, hey, I'm excited to be exclusive with you. Yeah, I mean, that's it's all good.

And at the same time, if they say no, then it sheds like to me that they're just not that into me, So why would I want to go down that road anyway.

So it's a really good kind of litmus test.

It is right when you when you when it's the right time, it's a perfect time to have that conversation.

And yeah, I agreed, So let's okay, So let's talk about this so a lot of the men that I've dated, including like my ex husband and different people, like supposing they're dating these younger girls and they have had vasectomies. So all of a sudden, you see a couple of

Do I not?

And it's interesting because a lot of times, all of a sudden, what I would assume would be so sexy with a young thing is that she's probably you know, you know, you know, for lack of a better word, banging you six ways to Sunday every which direction, and you're like, this is the greatest thing in the world and not my uptight wife, And all of a sudden, she.

Wants to do it. She's going to get the cankles and she's going to get all this and you're like, oh no, no.

So I've seen people like break up with that situation and like literally move into another situation.

Yeah, I mean, well, I want to make sure I understand the question.

But yeah, I've seen I've seen guys that said they said they didn't want to have any more kids, but then they were they still had like sperm stored and they were dating this one and they said, no, I'm not having any more kids, and then a letter came in the mail and their girlfriend was like, I thought you didn't want to have any more kids, right, So there are guys who are having trouble being honest.

Through that process. For sure, I would say.

If the guy is serious about the girl and he's and he says I don't want her, I don't want kids, then she she would know he doesn't want kids, or he's getting a reverse vasectomy, or they hope.

They're going to change his mind.

And I see that a lot.

Yeah, bad, bad idea.

If a guy says no, I don't want kids, for the women out there, just listen to that, and uh, don't assume you're going to change his mind.

That is not a great strategy.

So a woman named Nancy wrote a question, and I know we are this last time, but I do think it's something that's on a lot of people's minds. So she writes, I can't cook.

Is that a turn off?

Yeah?

Not to me.

I mean I said, I think maybe if we dial it back, maybe to the fifties or something, and people were like, oh gosh, the most attractive thing to me about a woman is you know, a great home cooked meal. I just I don't know how that can be in the top twenty things that attracts you to the woman. Like for me, there's a lot of other reasons to be attracted to somebody. They make you laugh, you do things together, you are, you have chemistry, you have whatever

It's a nice little plus.

It's like it's like it's like a cherry on top, But if you don't have the cake and the icing, the cherry is irrelevant, I guess, is the best way to.

Put totally agree. So you're in your fifties, your kids are older.

Do you and your friends want to get married again or do you feel like you just want a partner that maybe wears a promise ring, Like, do you feel the need to if you're not going to have children and maybe not necessarily share money, do you feel the need to get remarried?

Is that something you're looking for? Collectively your friends are looking for? What's the marriage conversation?

Yeah, I have.

I mean I have friends that are in both camps that are in their fifties. I would say there are some who are like, you know what, I've got kids, they have kids. We're just gonna kind of, you know, like you said, be promised ring, engaged forever and not worry about the marriage part. And they're happy as a clam. And both people are happier at least they say they are.

The being married part really was.

Like an important way to solidify their commitment to each other and like show that to the world. And they both were super into it. So they're both camps. You know, I don't know there's a right or wrong answer there. It's only wrong when the two of you have a different a different plan, right.

I didn't think right or wrong. I was just more curious what the temperature is. You know.

It's interesting because one of the things, you know, so my kids are in their twenties, and one of the things that everybody's talking about, you know right now, which kind of makes a lot of sense, is is having everybody sign a prenup right, like even though they might be you know, making two dollars if they even have a job, which is hard to get right now, and they're getting a full allowance from their parents. Is actually when people are getting married prepping a prenup right, nobody

I would think, yeah, yeah, I I mean, I agree with you.

I think people that spent you know, decades together and raise kids together, one person can't come out of it, you know, happy as a clam and you know, financially, you know, just live in their best life and the other person's feeling stressed and struggling.

I don't, I don't. I don't think that is a is a good outcome.

Right, So when people are getting married in their twenties and thirties, you know, it doesn't seem like the prenup is necessary unless itch, unless it has you know, unless it changes over time. Right, if you spend two years with somebody, it's one thing, five, ten, fifteen, twenty, it has to evolve over time versus just this is the agreement, no matter when we split up.

I don't know that that works very well. I will say the reason that, like my father got remarried you know, late in life. I guess he was in his sixties, right, and and he in order to kind of protect his kids and grandkids, like so you see a lot of people doing it in their sixties and you know, fifties sixties having prenups mostly because they have kids and they want to make sure things kind of go to their kids if it doesn't work.

But I would say for people in their you know, twenties and thirties, make sure that the prenup has has kind of time based changes.

So I have two more questions from two different listeners. Number one is.

Thoughts on you know, so one of the trends that is, you know, kind of big right now is not just separate bathrooms, which I actually think makes a lot of sense, separate bedrooms.

There's been a.

Lot of articles of that.

And I also think once you've been divorced and you haven't slept in the same bed, you know, seven days a week with somebody, kind of hard to kind of go back to that, right, Like my friends and I joke around about it all.

The time, like you know what I'm saying, like I want to turn on my TV in the middle of the diet or whatever. So what is your feeling on that?

And do you think the sleeping in the same bedroom for you know, the relationship health and and all that is really important, Like what's your opinion on.

Yeah, I don't, I don't. I don't think it's critical of all.

I mean people I know people who are they live three minutes apart in two different houses, right, and they've

They're so far apart the bed and there's like pillows between them and they're like literally like I was dating this guy and I was just I needed sleeping the same bed as I mean, if I was like waking up at five am, I was like running downstairs, you know what I'm saying, Like I couldn't gone out that that's fast enough.

So that's the other thing.

Yeah, I actually think there's almost you can probably do a study to prove that you have more chemistry and more run if you're in different bets. Right, So I probably lean a little bit towards that. But yeah, not I think whatever works, But I would say people should try it. They might find that it's kind of it's kind of fun to be invited in or have somebody sneak in who you didn't eangeable visits.

It's like conjugal.

Yeah, that's it adds a little element of surprise versus just the same thing every day.

It becomes so formulae and it just becomes so banilla.

Right.

Okay, so my final question, Okay, how long have you been single for?

Yeah?

I have been.

Single for about four years since my divorce.

Is that a function of you've had a lot of different experiences, all of which have value, right? Or have you just not met the right person that has made you want to lock down? And what would you say in the four years, has been your longest relationship or has it just been these like kind of situation ships.

Yeah, I mean, I I don't. I guess I would say I don't.

I don't subscribe to the theory that if there's somebody single in their fifties that they are necessarily doing something wrong. I think we all kind of grow and evolved differently at different times, and I would say, you know, it kind of takes what it takes to get you to the different parts of your life where you're into things that fit you better at different parts of your life.

I don't. I don't think any of those things are a black mark. Yeah. For me personally, I would say I am being.

You know we talked about this in the last episode, is that I think having boundaries and setting a low bar are are things that can get you into real trouble in life. It did for me and uh, and maybe it did for other people out there that are that are listening. So yeah, I would say for me, I'm I don't think being in a rush is as important as having boundaries, having a very high bar for your like for your partner. You should be excited about them.

It's a marathon.

This is not a spread like if you have someone who super connected to you, it's going to work out, Like you don't have to worry, like you've like there's no rush like, you found this person, it's going to work out. Your connection is amazing. So so you know, rushing it or going slow is not what determines success. It's finding that right person that determines the success. So it's like, yeah, for me, it's not about timeline or strategy.

I totally agree when I see people, you know, things out start fast typically end fast.

Right.

So I'm watching a friend right now who just starting dating somebody on an app and and I tell you, like they've met the kids, and it's like it's like the love bombing. And by the way, both of them, it's like they've literally fused on some sort of a wound where they're like imprinted on each other. And I'm sitting there and I'm like whoa. And I'm you know, no judgment to each his own. I hope it goes the distance.

For sure.

And there are those, you know, fairy tale situations, but I'm watching this thinking that would terrify me.

Yeah it is.

And I could say I had I've been in that situation where you you've been in kind of an accelerated relationship like you said, love bombing and things are happening too fast, and it's a it's an addictive it's a high that that merging and that kind of love bombing and moving too fast can be really it can be really attractive and a toxic. It's intoxicating. It's like a drug. But just like drinking too much, it is not the

That's that's my two cents.

Well, I have to tell you this has been so informative, and I'm sure our listeners agree, and I'm hoping that we can do this again because as we're all continuing to navigate this new situations, new questions, and to have the ability to you know, kind of dial into you and actually get the you know, we all sit there and we're like, well, what do you think this means? And let's analyze this and why is why does he goes to me?

And why didn't he call me? And why did he say this? It's you're not going to call the guy, right, You're not like, oh, why didn't you call me?

Or like it's better for us to call you and say hey, like try to you know, dissect for me what was what happened here? Or what's going on in this guy's head? Right, and so I don't make the same mistake or or we understand where did I go wrong?

Well, now it's super fun to me for me and I love being a part of the conversation giving the guys perspective. It actually shouldn't be that complicated, but unfortunately it is. So I'm very happy to be part of it.

So thank you.

Thanks for It's all kind of fun, right, I mean, you think about it like, it's it's all opportunities, the people we meet. It's never a waste of our time. Our time is just you know, it's we have time to meet good people and have interesting conversations.

We never know why.

We meet somebody.

You know, maybe all of a sudden you meet somebody and they're not for you, but all of a sudden, you know your child was looking for a job in that field and there's an introduction there, or.

You know, it's yeah, I agree I think, uh, I agree, getting just getting out there and trying things, learning from them, trying new things. Just the only, the only, the only mistake you can make is just is not not putting it out there and not trying like, don't don't you know, hol up and read a book every day.

You got to get out there and make it happen if.

It's important to you.

Right, A lot of people, I have a lot of friends, they just been burned and they just feel safer at home and they're just not looking, you know, to kind of put their out there.

But my dad once taught me better to have loved a little than never to have loved.

It at all.

Yeah, I agree.

Look, there's bad people out there in the world, but they're equally as many kind, generous, beautiful people out there. So getting burned is no reason to stay out of the game. You've got to there's tons of beautiful people out there that are super kind and supportive, and go out there and find them.

On that note, you will definitely attract one of those people because you are a really special, really special guy. So JD, I want to thank you for coming back on again to give our listeners some more insight and tidbits on how men think super cool to hear very informative. Do you have a question or need some advice from a single man, Email us or call us. All of the information is in the show notes. Follow us on socials.