How Does He Learn to Be Single Again? | #tinder | #pof


Dear Doc,

I’m about to turn 35, and find myself single after 12 years of being in a relationship. My ex and I met in college on a study abroad, and were friends (with benefits) for many months before we became exclusive. That friendship developed, evolved, and after six years of dating (four living together) we got married.

We were married for another six years until she suffered the loss of someone very close to her which ended up impacting our relationship greatly. We saw a therapist, both together and separately, and tried very hard over the course of nearly two years to rebuild the relationship, but ultimately we grew apart and decided to divorce. We remain friends to this day, but now I find myself single, and if I’m being honest a bit scared of it. We were separated and living apart for the last 1.5 years of our marriage, so it doesn’t feel like I’m coming right out of a relationship anymore. The pain of saying goodbye to my marriage has come and gone, and I finally feel ready to start exploring life again as a single guy. But unlike last time I was single (college) I’m not constantly surrounded by new people. Hell, last time I was single apps like Tinder and Bumble didn’t exist! I have joined the various online apps, and have been on a few first dates.

The first dates went about as expected given that I was new to online dating, and really dating again in general. The first date had great conversation, but lacked attraction, the second date there was attraction, but the conversation lacked some chemistry, and the third-first date had chemistry on both fronts, but external factors with family (she has a kid, and my family had some health issues) caused a second date to be indefinitely postponed until things just fizzled.

So I’m reaching out to you and your audience to better understand how one starts over in this brave new online world. With work, trying to start a new business, and maintaining healthy habits at the gym my time is limited, and it’s hard to motivate myself actually go OUT and meet new people. There are plenty of women I find attractive at the gym, but my assumption has always been that these women probably get hit on plenty there and just want a place where they can zone out and do their thing, much like I do at the gym. That said, I’d be totally okay with being hit on at the gym, so perhaps I’m putting up barriers for myself that don’t exist.

As you can probably tell by now, I’m not quite sure how to be single guy looking. I’m not really looking for anything too serious, but also not relegating myself to simply hooking up with people. That said, starting with something casual would be okay. Part of that long separation in my last relationship also means it’s been quite the stretch since I’ve had sex, and I’m not going to lie, I miss it! But where to begin? Datings apps, going out, speed dating, the gym . . . do I just cast a wide net, or is there a strategy to singledom?

Any and all help is greatly appreciated,

Starting Over Single

I don’t have much advice for you on how to meet people, SOS because honestly, you don’t need it. You’re actually doing everything right: you’ve gotten on the apps, you’ve been talking to people and you’ve been on more than a few dates. That’s all precisely what you should be doing, my dude, and you’re having quite a bit of success with it. Your experiences thus far are fairly typical when it comes to online dating. As I’m often saying: humans are built for face to face communication, and there are many things that are requisites for attraction that you can’t pick up on without being in their physical presence. As a result, you’re going to meet people who seem great on paper, even on messaging apps, but who you just aren’t compatible with in person. Dating in general is a numbers game; you’re going to meet more people that you’re not right for than folks you are right for. That’s not a problem with you, that’s just life and that’s fine.

The bigger issue is that you seem to be intimidated by the magnitude of it all. That’s why I want to reassure you: you’re not the only person who’s had to go through this. Hell, you’re not the only person ever to write to me this month wondering about how you get back in the game when you’ve been out for years, even decades. It can feel incredibly intimidating — like you’ve just been revived from cryo-stasis and now the world is so alien to you that you’re practically catatonic. But you have an advantage here that lots of other folks in the dating scene don’t have.


You’ve done all this before.

No, for real. The fact that you’re coming from a 12-year long relationship means that you’ve been there, done that and seen so goddamn much. You have far more relevant experience under your belt than so many of your compatriots out there.

The key is that you are looking at things from the wrong angle. Guys who are single and on the scene tend to focus entirely too much on the early days of dating. They’re looking at the mechanics of the approach or focusing on where to meet people, when these are literally the last things you need to worry about. Approaches feel like they’re important because they feel so immediate and they can feel far more consequential than they actually are. After all: you’re going up and making yourself vulnerable to a relative stranger and hoping to convince them that they want to start a romantic or sexual relationship with you. Apps like Tinder and Bumble can seem to make it even more intimidating; now it feels like things move faster than ever, oh brave new world, etc.

But it’s not true. Things only feel like they move faster than they do because a) we’re all more honest about what we’re doing and b) people focus on the more salacious stories about hook-up apps and swipe right for blowjobs right now and not about all the slow-burn relationships that started right alongside all that casual sex and one-night stands.

Dating apps are just a vehicle for meeting folks. It only seems crazier because it’s giving you access to a volume of potential partners you didn’t have last time you were single.

In reality, approaches are actually the least important part of meeting someone. People who put all of their time and focus on learning how to make approaches get good at approaching people. What they’re not good at is connecting with them. Folks who are the most successful with women aren’t the inveterate approachers who can start conversations with anyone, they’re the folks who know how to talk to women. Guys who can talk to women, help women have a good time and generally make them laugh and feel good are the real MVPs of the dating scene.

And you already have those skills. You know how to talk to women. You have nothing to be nervous about.

I mean, my dude. You’ve been in a relationship with someone for more than a decade.  That means you have had so many weird conversations with your ex that seem like nothing. Why? Because you had confidence in yourself, in her and in your relationship. You know you’re capable of opening up, being vulnerable and knowing that folks who care for you will be ok with it… because you’ve done it already. It feels scary and intimidating because you’re picturing all the ways things could go wrong. But in reality, you’ve been on this ride before. You know a lot of what to expect.

That’s why worrying about where or how you’re meeting people is less important than what you’re doing after you meet them. Having those great conversations and first dates are part of how you find the people who are right for you. You screen for chemistry, you screen for compatible lifestyles and you look for people who want what you have to offer as much as you want what they have.

And you do that by simply talking with folks. Getting to know them. Telling them what you want and are ok with and what you aren’t up for. Which you’re already doing. So honestly, my only real advice for you is “Keep doing what you’re doing, because you’re doing great.”

You may be a little rusty at first — this is a skill set after all — but you’ll get back into the swing of things far faster than you realize… in no small part because you already know how to talk to women. You know there’s nothing to be afraid of. So focus on presenting your best, most authentic self to them and meeting people who you click with.

But as a general word of advice: don’t spread yourself too broadly. You want someone who craves you, not someone who thinks you’re alright. Being broadly but shallowly appealing isn’t nearly as valuable as being deeply desirable to a smaller group of people. Life’s too short for dating people who’re only lukewarm about you.

Good luck.

Hello, Dr. NerdLove.

I’ve heard good things about you, so I’m hoping you could help me with what I’d describe as a social anxiety problem.

I’m a 20 year old cis man, going to be 21 in April. I’m currently living with my family and working part time. I’m a bit overweight but I am trying to diet, and I’m hoping I can manage it with my sweet tooth.

One thing that’s really bothered me basically my whole life is that I have Asperger Syndrome. This made it really hard for me to handle myself in social situations. It got especially rough during middle school and high school. I’d throw tantrums, I’d break down over simple things, and worst of all, I was terrible at making friends. I didn’t really get a chance to hang out with anyone until my last year of high school and by then they were all busy with college stuff and there wasn’t that much time left to spend.

Right now, my social circle is about zero. I think the last time I really hung out with anyone was last year or the year before. A lot of times, I’m okay by myself, but it can get lonely at times, not being able to actually be in the same room as someone around my age. It can get pretty lonely. I’ve reached out to some old friends before, one quite recently, in fact, but it can feel awkward for me since it’s been ages since we talked and I’m not sure what to say. And sometimes they just don’t talk to me and I have no idea why.

And that leads me to more recently where… I guess I’ve been bit by the sex bug or something. I’ve just been really interested in having sex with someone. I’ve never had it before, and there are several people I follow online who aren’t afraid to talk about what they’ve done. I know it’s not a race or anything, but just hearing about it makes me wish I could experience what they have.

And then there’s a whole issue of intimacy. I feel like I’d want my sexual encounters to be a more consistent, one-to-one thing. I’ve read some of your responses and articles regarding friends with benefits, and I don’t know if it would make me feel shallow. Like, part of me is thinking “sex can just be an activity that two people or more can enjoy together, regardless of if they’re into one another, just good friends, or whatever.” On the other hand, there’s a part of me that feels like with sex, you kind of cross some line regarding friendship, like there’s something more going on.

I’m really on the fence about it and I don’t know how to feel. Like, I feel like if I found a person willing to do it with me, I’d want to continue with that person and I am almost afraid of not knowing what to do with this woman and where to go down the line. Would it feel less special? Would things get awkward between us? It’s a lot to think about.

So anyway, between dealing with my loneliness on occasion, having a small social circle, trying to reconnect with old friends, “being bitten by the sex bug” as I put it, and having so many damn thoughts about the damn thing, I suppose my question is, “Is it a good idea to put myself out there? And if so, how?”

Like, for real, I don’t know where to start. I live in a suburban neighborhood, so there aren’t exactly any trendy nightclubs or bars in my area. I mean, there might be if I drove around, but again, basically no idea where to look. I know there are sites like, where you can find people with similar interests, mainly stuff like gaming, Internet stuff, and other pop culture stuff, but I don’t know if that’s my only option. If I were looking for a girlfriend, would I try online dating? There are like a million sites and apps to choose from. I don’t know what I’d choose. Plus, I’m not the most physical of specimen, so I’m kinda worried that would hurt my chances.

As for the sex thing… honestly, I’m not 100% sure what I want. I don’t know if I’m ready for a serious relationship yet. I still want to build my social skills a bit. And at this point, I’m not sure FWBs would be a good idea either. I’m not sure if it would end well for me or her and the prospect kind of scares me. Hell, maybe the whole “sex bug bite” thing will pass in… I don’t know how long. Days? Weeks? Months? I don’t know.

I’m not sure what I want, but I guess having a group of friends would be a good start. And I’m really unsure how to proceed. Maybe building up my social skills? But I don’t know how. Maybe I’m not ready for sex at all because I’m afraid I’ll let her down. Or, like I said, maybe these feelings will pass in a while. Thinking about it now is kind of nerve-wracking. I’m really unsure how to go forward and you tend to give sound advice. Can you think of a course of action for me to take? Or just any advice in general? I’d appreciate it. Thanks for taking the time to read this.

Dazed, Desiring & Desolate

You’re overthinking things, 3D. 90% of what you’re getting spun up about are, in the scheme of things, fairly minor. You’re putting a lot of thought and energy into minor details and letting the sheer magnitude of it all overwhelm you. Practically speaking, it’s all much simpler than you’re worried about. Like I just told SOS: most of building a relationship with someone is just about connecting with them, getting to know them and finding the person who’s weird matches yours.

The difference is that you’re coming to this from a very different place, with some unique challenges. The key is to focus your time and attention on the right areas that’ll put you on the path to getting what you want.

Here’s my question for you, 3D: how is your life right now? How you feel about yourself and your life goes a long way towards having a successful or unsuccessful social life.

You mentioned that in high-school, you had issues with getting overwhelmed and how being stressed and overstimulated could cause problems. Do you have that under control? Are you in a better position to manage your emotional needs so that you feel in control and confident? The more you feel that you have a handle on that, the less anxious you’ll be in social situations. This means that you’ll be in a better position to talk with folks without feeling like you’re having to divide your attention.

Similarly, how are you with talking to people and making friends? The skills involved with making new friends are fundamentally the same as the skills you use to find a parter; the only difference is the end point of the relationship.

This is important, because you’ve mentioned how lonely you’ve been. That, I think, is the issue you should try to resolve first. Coming to dating when you’re chronically lonely makes things much harder and more frustrating. It’s much harder to find what works for you when you’re feeling such a cavernous lack. You’re more likely to chase after potential matches who are simply not right for you because you feel like you need to focus on them or else die alone and unloved.

Having some good friends — your Team You, as it were — is important to your social success on a number of levels. To start with: you have people in your life who love and care for you, which is important for your emotional health and well-being. Having those friends helps your self-esteem, it gives you people who support you and cheer on your successes and who’ll help you recover from your failures.

They also help you meet new and awesome women. Having an abundance of people in your life — including female friends — helps make it easier to meet folks who are your kind of yum.

But what about the question of sex? Do you go for FWBs? A casual, no-strings relationship? A monogamous partner? My answer is: yes. All of the above. Or none of the above. See, the only person who could know what’s right for you is, well, you. As you give yourself time to grow and focus on those social skills — and that social circle — you’ll be getting to know yourself better. And when you’re on more stable footing, you can try different options. You can try a casual relationship for a bit and see if that brings you satisfaction. You can date around with an eye towards something a little more long-term and see if that’s right for you. Figuring out what you want is going to involve taking chances. You’re going to have to do some trial and error to see what does and doesn’t click for you.

You may find what you think you want isn’t what you need. You may find that the things you actually want are so night-and-day different than what you could possibly imagine now.

Yeah, it can feel scary. You’re going to have to take chances and risk being hurt; there is no reward without risk. But the rewards not only are worth the risk, but you’ll quickly discover that failure may suck… but it won’t destroy you. And that knowledge will help you build your confidence and give you the extra motivation to make your move when the time comes.

For now: don’t worry about sex. Masturbate, get to know your body and don’t get hung up on “being good enough”. Focus on meeting people in general, making friends and living an awesome life. Doing this will not only make you a more confident, more assured person, but it’ll help bring people into your life… almost without effort.

Don’t worry about trying to make up for lost time. Your past is merely prologue; the first act of your new life starts now. And it’s going to be a good one.

You’ve got this 3D.

Good luck.

Previously published on and is republished here under permission.



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