How Do I Turn My Dateless Life Around?

Estimated reading time: 13 minutes

Dear Dr. NerdLove: ’ve been reading your website for a while now and figured it was time I shoot a message your way, especially as right now I’m at my wits end for what to do with myself.

I’m a late twenties male who hasn’t had a date for the last ten years. I’ve tried, of course, but to no avail. It’s very frustrating, particularly as there’s no real reason why I shouldn’t be able to find someone to spend time with.

So what have I got going for me? I’ve got the basics down, like a roof over my head and car. I have a career I’m extremely proud of, and passionate about, and which allows me to live a lifestyle that I enjoy. I’ve got my health, including working out regularly, and I make sure to look after myself otherwise with clothes that fit, grooming, cologne etc. I’m caring, thoughtful, intelligent, and I’m a great listener. I enjoy talking to people and getting to know them. I’m supposedly good-looking; I’ve had random compliments throughout my life to that effect, and I’ve been consistently rated as a 9 on Photofeeler. To put myself out there, I’ve been to salsa classes, board game groups, pub crawls, ice-skating, concerts and other meetup events. I’ve tried dating apps on-and-off.

I’ve yet to make a friend throughout any of this, let alone a date. I get along with people, make them laugh and generally give off a good impression, but it never translates to anything meaningful. I’ve never been approached by a woman, and they generally avoid talking to me in group settings. I certainly have never noticed any sign of attraction. I just go to events, talk to people, but in the end I’m always alone. It’s got to the point now, that I don’t bother to go out.

Just the other day I had a colleague say I was handsome and that I must have had plenty of women in my life, and not long after that, a female colleague said it was a shame I was single because I’m “good-looking and a great guy”. It’s all very confusing when people seem to think highly of me, but I’ve got no romantic or social prospects…and it hurts.

To top it all off, I’m now scared of being the type of guy who will eventually get settled for. I’ve missed out on dating when I was younger, and I can’t see my luck changing for the better.

I’m in therapy, so here’s hoping that eventually helps me, but until then, I just need to get things off my chest, and maybe get some guidance in the process.
Thanks.

The Lost and the Lonely

OK my dude, I get a lot of letters like yours, and I chose yours because it’s a prime example of some classic mistakes I see men make all the time. So I want to preface this with the understanding that this isn’t just about you, so much as the collective you and other men who’ve found themselves in the same boat.

Similarly, I want to make it clear: this is going to be blunt. This is going to be unpleasant. But I promise you: make it to the end, take it in, and you’ll be in a much better position than you’re in now.

So with that in mind, I want to talk about what I’m not seeing in your letter: you don’t say what you do. Not “what job do you have” or “what actions are you taking”, but actual verbs. Actions. Behaviors. Actual, demonstrable steps you take with others.

When I look at this list, I see two categories of descriptions. There’re the qualities that’re directed towards yourself – dressing well, taking care of yourself physically – and that are passive, such as being a good listener. And hey, that’s all well and good; taking care of yourself, working on your style and presentation is important. But it’s not active. It’s directed inward, not outward. Yes, being conventionally good looking helps. Having a strong sense of style and getting your grooming on lock helps. But it’s not going to do the work for you. If you think about it in D&D terms, it’s giving you an advantage on some of your rolls; it’s not going to draw people in, in and of itself.

Similarly, “being caring” and “being a good listener” is nice… but that’s a very passive thing. It’s important, yes; these are things that people are looking for in relationships. But it’s not only not the only thing, it’s not something that draws people in. Telling someone you’re a great listener isn’t going to make them want to date you, any more than being “a really nice guy”. Those are, honestly, the sorts of things that people expect to come standard. The fact that they often don’t is something of an indictment on how men are raised and taught, sure, but it’s not going to bring someone in.

If you’re a regular reader, then I’m sure you’ve seen me talk about passing The Grimes Test. If you haven’t, then let me run you down a quick version: Grimes is a kaiju made out of toxic waste. He’s relatively cute as far as toxic waste monsters go, he has a job, he has is own place to live, but he doesn’t have much of a life outside of work. Grimes has never hit a woman, he’s never harassed her or sent pictures of his genitals to someone without their express consent. The Grimes test is this: what do you have going for you that Grimes doesn’t already have, that would make women want to date you instead of Grimes?

What you’ve described about yourself thus far doesn’t pass the Grimes Test precisely because it’s very much about an absence of negatives, rather than an abundance of positives. Grimes is the baseline; you want to date, then you need to do more than the baseline.If you want people to want to date you, you have to bring things to the table that go beyond just inherent qualities.

To put it another way, it’s a little like the quote from Glengarry Glen Ross: “Nice guy? I don’t give a shit. Good father? Fuck you, go home and play with your kids. You want to work here, close.” 

You aren’t closing. You aren’t demonstrating to people why they should like you or want to talk to you. You have to do things that actually bring value to their lives – things that aren’t just “sit there and listen while you talk about your day”.

If we go through the list of things you’ve done, I see a list of places you’ve gone and hung out. I don’t see you saying “and while I was there, I talked to X people, made Y connections, invited Z people to do things”. I see you say that nothing “happens”, or that women don’t approach you or ignore you in group situations. And that’s the wrong way of looking at things.

You can’t wait for folks to do the work for you. Yes, having women approach you is nice when it happens – and there’re certainly ways to increase the odds of it happening – but you can’t rely on it. You have to be willing to take the initiative, take risks and put yourself in a place to get rejected.

Now, I can hear you, and other guys like you, say “well how do I do that?” And so let’s take a theoretical example from your list of activities… the board game group, let’s say. You go to one for the first time and there’re lots of folks there. Ok cool… are you chatting and having fun with folks? Are you making a point of connecting with people, maybe setting up a game and saying “hey, want to get in on this?”  Or are you taking a more secondary role, where you’re waiting for people to ask if you want to join them? Are you being an active participant in those group conversations, or are you just sitting there, hoping someone will ask you questions?

If you go over to people, introduce yourself, get to know them a bit, that’s going to work far better than hoping that they notice you or bring you in. That’s going to signal that you have confidence and belief in your own value. If you’re waiting for other people to do that for you, then you’re not showing what you actually bring to the table.

Similarly, being the person to invite others to play a game goes a very long way towards establishing yourself as someone who brings things that people value to the table. You’re creating a situation for them that is fun, where they’ll enjoy themselves, instead of letting it just happen. If you were to say “Hey, I brought a copy of $GAME, have you ever played it before? No? Awesome, here, let me set it up, it’s really fun,” then you’re creating an opportunity for these relative strangers to have a good time with you – something that is incredibly attractive and appealing. They’re going to associate those feelings with you, because you’re the one who created the situation for those fun times to happen. They’re not going to say “oh the GAME is fun”, they’re going to say “Wow, Lost and Lonely is a cool guy, he brought a fun game we’d never played before.” 

Afterwards, are you connecting with people? Are you committing to coming a second time and a third,  becoming a regular at these events? Are you saying “hey, I really enjoyed talking with you, can I add you on Facebook/Instagram/WhatsApp/whatever?” Are you setting up opportunities to hang out again? Are you saying to people “there’s this cool barcade that just opened that I’ve been meaning to check out, you should come with me” or doing things like maybe organizing a cook out or some other group get together?

If you aren’t, then you’re being passive, not showing what you have to offer and ultimately waiting for other people to choose you and do the work for you. that’s not attractive, that’s not helpful and honestly, you’re not going to get a lot of great friendships or relationships if you’re just hoping for someone to come and adopt you into the group. You don’t have to be the leader or organizer every time, but you do need to be much more active than what I see from guys in your position. 

What does it look like if you’re not being the organizer? Well in that case I can give you an example from my OWN life: how I joined a popular podcast. When Spill.com (RIP) had a fan meetup at a bar in Austin, I went and chatted with everyone, especially the talent – Chris, Martin, Cargill and Korey. Chris and Martin and I all got along well when we talked, and Chris invited me to come chat at the bar where he worked; he had some questions about some animation work I’d done. I made a point of coming by semi-regularly to hang out, drink a beer and talk movies. Over time, we become friends and eventually because we had good chemistry and I clearly had no problem being a chatty bastard, he invited me to be a guest on the League of Extremely Ordinary Gentleman.

None of that would’ve happened if I hadn’t deliberately made it happen. Yes, Korey and the others arranged the meetup and Chris invited me both to the bar and to the podcast, but it happened because I made a point of connecting with them, making them laugh, telling fun stories and generally being someone they enjoyed talking to. I didn’t wait for them to bring me in, I went up and introduced myself.

Now to be clear: I didn’t have an agenda for any of this besides making friends. I just really enjoyed hanging out and talking with folks whose work and creativity I admired. But I was proactive about it. I was bringing value to the interaction by helping them have fun and being fun. And I would do things like help out with cleaning or set up, bring drinks to recordings, put on parties and get-togethers, all of which helped cement our friendships.

Are you doing any of that? Because if not, then there’s your problem. If you’re at a bar, you have to be willing to make the first move and risk rejection; otherwise you’re not going to be able to flirt, joke and have fun. You’re not going to have opportunities to bring people in or show them a little of what you have to offer.

It’s also worth noting that all of this happened over time. When it comes to meeting people – whether you’re looking for platonic friends or romantic partners – one of the most important factors that leads to success is repeated exposure. That is, folks see you frequently, get to know you over time and become comfortable with you. Regular exposure breeds familiarity. Familiarity breeds both trust and affection. Trust and affection breeds relationships.

We all love the idea of love at first sight or a meet cute that immediately leads to dates or something, but that doesn’t happen often. Most of our relationships, platonic and otherwise, come about because we get to know people over time. This helps build a relationship that can blossom to attraction, but also makes you more attractive to people as they get to know you.

If you’re only going to these events once and bailing when it doesn’t immediately net you a date, or not going often enough to become known, then you’re essentially sabotaging your own efforts. You will do much better if you become a known quantity and allow folks to get to know you, instead of looking for immediate, incredible success right off the bat. Everyone loves the idea of the player who rolls into the club and immediately attracts all the ladies, but in reality? The vast majority of our relationships come about when we spend time with folks we’re compatible with.

So if you’re tired of being alone, then you need to start taking more concrete steps. You need to commit to more than just a one-off MeetUp or showing up once or twice to some gaming event. You need to be proactive about not just introducing yourself to other people, but making connections happen. This could be by organizing game nights, setting up cookouts, even getting people together to do something crazy and fun like having a pillowfight in the park or getting people together to do Segway tours of the city or something. Even if you’re not the organizing type, then you should be making a point of proactively meeting people, staying in contact with them and building your connection with them.

And, importantly, you need to be active in bringing value to their lives and showing what you bring to the table. This may mean dinner parties. It may mean being the person who shows up to help set up the event and clean up afterwards. You might be someone who knows where the fun new bars or interesting restaurants are, or who invites folks to come watch the game or the MMA match or otherwise arrange group hangouts in fun places.

It could mean connecting disparate groups of friends because you know that Dude from Friend Group A would really click with Friend Group B or that Woman from MeetUp Z is looking for work and Dude from Friend Group B needs someone with her talents.

And if you don’t have those qualities or you aren’t finding ways to show them off or utilize them? Well either you actively go out and cultivate them, or you put in the work of figuring out how to make it happen. You may have to think outside the box a bit or get creative… but those make you more interesting, more unique and thus more fun to be around.

Please notice very carefully that the common denominator in all of these is how you make people feel. Part of bringing value to people or showing what you bring to the table is to recognize it’s not about material goods or showing off. It’s about the emotions you inspire in folks through those actions. The better you make people feel, the more they enjoy hanging around you. The more they enjoy having you around, the more they’ll prioritize time spent with you instead of other people.

The more you show folks why it’s good to have you in their lives – even if that just comes down to “you’re really fun to talk to” – then the more success you’ll have. But you have to do it in a way that you actively make happen, instead of hoping that others will do the hard work first.

Good luck.