Estimated reading time: 15 minutes

Hey Doc!

So, a few weeks ago I went out for karaoke. I had fun singing and ran into a couple of friends of mine at the bar. I ended up chatting with a woman at the bar who I seemed to get along with. I didn’t really think anything of it at first, but I figured this would be an opportunity to practice some low-stakes flirting. Just see where things go. Long story short, we both had a few drinks in us and she came home with me.

We had a good time, and she really seemed to enjoy my company. I was actually really surprised that she thought I was charming, smart, and had my shit together. My house was kind of a mess at the time, but she said that my place was clean compared to some of the other guy’s houses she has been to. We both agreed that this was a strictly casual encounter. She’s appreciably older than me, and she seems to enjoy her independence and sexual freedom. On top of that, if I’m being honest, I wasn’t all that attracted to her. We hung out for a while in the morning, she told me she had a great time and that we’d probably see each other around, and I gave her a ride home. Things worked out pretty well.

This is the first time I’ve ever had a one-night stand like that, but I noticed that it is part of a pattern. It seems like when I do end up hooking up with someone, it’s someone that I’m really not all that into. It’s just that they’re interested in me, and they’re pleasant enough to hang out with, and one thing just kinda leads to another. In the past, I’ve hooked up with a few friends or friends of friends. It’s the same story, just with a bit more familiarity.

I’m pretty sure I understand WHY I do this. Maybe it’s not the healthiest way of getting validation, but it definitely feels validating, and I do seem to get a sort of temporary ego boost after something like this happens. It had been close to a year since the last time I had been with someone. I’ve been very up-front with all of the people I’ve hooked up with that it’s just a hook up, so it’s not like I’m leading them on. They’ve all enjoyed themselves, but mostly I’ve just found it entertaining more than satisfying, if that makes sense? What I don’t understand is why this seems to exclusively happen with people that I’m just kind “meh” on, in terms of sexual attraction.

I had fun and I’m glad that it happened, but part of me wonders why I can’t ever seem to hook up with someone who, ya know, actually does it for me? I’m not entirely sure what’s happening. Am I actually charismatic and attractive, but that just shuts off the moment I’m talking to someone that I’m actually into? Or am I just not my type’s type? I’ve had the same kind of approach with plenty of women that I was interested in, and it never really seems to work with them. Any advice?

Right Game, Wrong Players

And hey, if a young spry thing is offering some no-strings fun, why the hell not?

However, as you’ve noted: this isn’t the first time it’s happened, but it’s always correlated to being with people who you could take or leave, rather than people you found to be attractive. Those were people with whom you were invested in a specific sort of outcome and – unsurprisingly – that means that you’re going to be less present, less playful and more focused on the meta-conversation than what’s actually going on.

If you stop and really think back to those interactions, you’ll likely notice that you were relaxed and able to just vibe with them. Instead of measuring and choosing every word you say with great care while also monitoring their every micro-expression like you’re at the final table of the World Series of Poker, you can joke around, flirt, and just see where things go. You don’t have that drive to try to be perfect and impressive because if this doesn’t happen… well, it doesn’t happen. No harm, no foul, no dings to your ego or sense of personal value because hey, these didn’t count.

They also have the benefit of not tripping any sense of scarcity for you. Talking to these people for funsies or for practice feels safe because to your mind, there will be more in the future. If things don’t pan out, you’re not going to feel like you’re one step closer to emptying the hook-up bucket forever. So as a result, you feel freer and more empowered to take risks and take bigger swings, try things you might not try otherwise or say things that you might not say to your dream girl.

Of course, this also plays into confirmation bias; you’re going to give more credence to the times that this has worked out for you than the times that it hasn’t, simply because this is where your head’s at. The story you are telling yourself – the belief you’re reaffirming – is that you’re fully capable of hooking up with people you’re not into, so you don’t pay as much attention to the times when you were flirting with someone for practice and nothing came of it. The opposite is true for when you’re attracted to them; your belief is that you struggle and fail, and so you give more credence to the times you fail instead of noticing when things were going well. This is a prime example of what my friend Arden Leigh calls “hacking your confirmation bias” – making it work for you by choosing to believe the things that help you, rather than hinder.

What this should tell you isn’t that your charisma and charm shut off when you’re around people you like or that you’re not necessarily the type for the people you’re into. What it should tell you is that you have the skills to get people to like you. Your issue is that you’re struggling to apply them when you feel like it “counts”. This is very much a “magic feather” problem; the ability was within you this whole time, you just need to give yourself permission in order to access it.

Here’s the thing: while it’s understandable that you’re going to be more invested in hooking up with someone who’s your favorite flavor, you have to remember that they’re not different from the folks you are less attracted to. They’re just people, same as anyone else; the only difference is the level of importance you are assigning them. You’re ending up with a case of the yips because you psych yourself out before you even open your mouth. This is why the ultimate key is that you have to start training yourself to do something you don’t want to do:

You have to be willing to lose. And more importantly: you have to be willing to lose and not mind losing.

When you have that scarcity mindset, that fear that every rejection is a step closer to never connecting with anyone, you’re not playing to win, as it were, so much as playing to not lose. You play it too safe, too conservatively and too timidly; you’re not authentic and relaxed with them, and you’re not willing to risk the possibility of taking that big swing that you might take with someone else. But all that does is make it harder for you to find the people who are right for you.

The thing is: just because you find them attractive doesn’t mean that they’re compatible with you. They’re still relative strangers and you know next to nothing about them besides the fact that they’re hot. Part of why taking those big swings feels risky is that they’re inherently polarizing; when they hit they hit hard, but when they miss, they miss hard too. But that’s the entire point: when those big swings are in alignment with your authentic self, many of those misses will happen because the other person isn’t right for you. I understand that when it feels like you never succeed with the people you are into, it can be difficult to be willing to be selective and to risk filtering people out of your dating pool. But the people who aren’t right for you won’t magically change if you take more time; they’re still going to be wrong for you. Being more polarizing means that you spend less time, less effort and invest less into people who simply are a poor match for you. At the same time, it means that the people who are right for you will have a much easier time seeing that, because you’re putting it out there, up front and easy to see.

Taking bigger swings and bigger risks when you’re actually attracted to them is also going to be important because it’s going to help you fine tune what doeswork and doesn’t work. It’s one thing to luck into something that works most of the time. It’s another to figure out why it works so you can use it with greater skill, greater precision and greater success… things that can’t happen if you aren’t willing to make mistakes first, so you can learn from them.

And that can’t happen if you’re playing to not lose, rather than to win. Practice and scrimmage are great, but the point is to drill the skills into muscle memory, so you can pull them out when they count, not about picking up easy wins.

So as uncomfortable as it can be: you have to be willing to put the same attitude of “let’s see what happens, it doesn’t matter if this doesn’t work out” into your conversations with the people who make your limbic system sit up and sing “Helloooooo nurse!” as you do with the people who are just kinda ok. You have to be willing to risk getting shot down now in order to succeed in the future.

You’ve got the skills. You’ve got the experience. Now you just need to stop practicing and start playing for real.

Good luck.

Dear Dr. NerdLove,

I (41f) tend to be the pursuer in all of my relationships. When I see a man I find attractive, I’m the one to initiate a conversation, ask them on a date, arrange further gifts and outings, etc. In all of my long-term relationships, I was the first one to bring up moving in together and marriage.

In short, I occupy the role which stereotypically belongs to men. Generally, I like this and find that it suits me. I like doting on someone, I like taking care of them, and I like being forthright with my feelings.

But! Occasionally I would like to feel like I am the person being pursued, and that it’s something exciting. Yet my dating strategy does not select for men who want to do this. Left to their own devices, they just don’t, which is fine, nobody needs to be a mind reader. But when I asked my current BF if he would do this for me, he asked what exactly it would entail, and I told him that I wanted it something where we both dress up nice and he takes me somewhere new as a surprise, and he told me that sounded really stressful and high-stakes and he wanted to stick with what we usually do for dates, which was to pick a place to meet and then jointly figure out what we’re doing from there as the spirit moves us.

Anyway, fair. Still, what are the sorts of things I could suggest to him that would scratch this itch for me? He is clearly not indifferent to my presence, but his preferred way to show affection is through things like warm domesticity, bringing me tea and soup, cuddling up to me when we’re somewhere comfortable, discussing our feelings over poetry, that sort of thing. Which is great, and most of what I want in a relationship, except for maybe once or twice a year for something else.

Thanks!

The date-arranger

It’s easy to think that this is a sign that your boyfriend doesn’t care, is lazy or isn’t interested in being a full partner, and I’m sure a lot of people will leap to precisely that conclusion. However, I think your boyfriend’s told you exactly why he’s struggling with this, TDA, and I think that’s where the answer to your question lies.

It sounds like what you’re asking for is enough outside of your boyfriend’s experience that it’s intimidating – in the way that planning a big vacation can be intimidating when you’re used to weekend getaways or day trips to places within an easy drive. The more moving parts, the higher cost of entry and more unknown unknowns, the more you worry that you’re somehow missing some crucial piece that will end up bringing the whole thing crashing down.

The surprise factor is probably a significant reason why it’s intimidating to him. This is something that obviously would be important to you. Your boyfriend, wanting to please you, would obviously want it to go well. But if this is something that’s significantly outside of his comfort zone andsomething important to you, I can see how the worry that he’s going to mess it up might overload those particular circuits and so he defaults to the safe and the known.

I suspect that another part of the issue is that – again, because this is outside his usual MO – he isn’t sure what a successful surprise romantic date would look like. This is something that can come up, for example, for neurodivergent people with executive dysfunction issues; not having a clear idea of the end point makes it hard to even start in the first place. If the idea you gave him was as broad and undefined as how you framed it here, I could see how “I have no idea what this would look like” could quickly turn into “…and now I’m stupidly stressed out about it and the neurons won’t fire”.

In a lot of ways, it’s like how there is nothing more intimidating than a blank sheet or infinite possibility. If anything and everything is possible, then you end up psyching yourself out. You can end up spending hours and days on something only to realize that you’ve been going in the wrong direction entirely and have to start over from scratch. But if you have walls to bounce off of or limits to work within, you often find that your creativity is spurred to new heights.

This is why writing prompt exercises or themed warm-up drawings are helpful – you’re breaking through that initial blockage by giving yourself limits, which then gives more structure and direction to work with. It’s easier to generate the initial spark when you’ve got something to strike against, after all.

So, having some structure would help here. Dressing up is certainly one example of a limit to work with, but that can be a little too vague. Does dressing up in this case mean a step above business casual, if you’re both usually t-shirts and jeans types? Or are you seeing it as a coat and tie for him and a cocktail dress for you? What sort of activities are you seeing as being dress-up worthy? Are you more interested in, say, dinner at a fancy restaurant and a gallery opening? Going out for cocktails at a nice lounge and then dancing at a jazz club?

As much as I know you would like to be the one taken on a date instead of planning it, I think something that might help would be for the two of you to collaborate on an example of the kind of date you’d like to be taken on. While this wouldn’t be the sort of “honey, I’m picking you up at 7, wear a nice dress and cute shoes” surprise you’d like, it helps lay the groundwork and structure for future dates that he plans and executes for you. It gives more of an idea of the kinds of date you’d like to be taken on, which makes it easier for inspiration to strike. And if you both happen to come up with a list of ideas, locations, restaurants and venues… well, so much the better. Now he’s got resources to work from, which helps streamline the process further.

Now as I said: this would be the “ok, here’s an example” date, not the “Ok, this will satisfy my desire to be the one taken out on a date for this season” – the one that says “right, so that’s what it might look like” to him. So, with the initial experience under his belt, you can say “I’d like it if you could do something like that for me in the near future” – a reminder that you would still like to be taken on a date that he planned for you. 

So take some time and collaborate on a date that he can learn from, then turn him loose. If he’s the type who has a hard time planning for a nebulous “some time in the future”, pick a range of nights that would work for you; having deadlines or specific days can likewise help avoid the “whoops, I forgot” time-blindness too. It’s a little more initial effort than you’d prefer, I realize, but sometimes that little push at the start is what gets the well-meaning-but-unfocused over the initial hump.  Once your boyfriend feels a little more sure that he can pull this off successfully, it’ll become a regular part of his repertoire. 

Good luck.