How Do I Stop Overthinking My First Dates?

Estimated reading time: 13 minutes

Hey Doc,

Long time reader, few times writer.

I am a cis man in my early 30s and my question is quite easy but can also devolve into a 10pages letter, so I’ll try to keep it as short as possible, here we go:

How do I avoid feeling after a first date that the person is not interested in me, that I wasted her time and there is no way she’d want to see me again, even though she never indicated anything of the sort?

I want to preface that I know this has nothing to do with the person I go on a date with & I do not adhere to the incel and red pill BS, this is a me problem that I need to overcome.

To give you a little more detail about who I am, I am a twice sexual assault survivor, I’ve worked through it and taken the necessary steps to heal from it, I’d be lying if I said that it doesn’t impact how I see my own libido (an entirely different can of worms) and my own worth. I am someone quite sociable, never had a ton of friends but the ones I have are quite close and dear to my heart. I don’t have a problem with meeting people or talking with women.

For two years I’ve been extending my social life, making friends with a few people (men and women), for the past 5/6 months I have been getting back into shape, not that I was fat (always been a gym rat) but I drank a lot and ate a lot, (homemade meals but still), so I cut down my drinking, changed my diet (still kept the cooking part though) and lost almost 8.5Kg (18lbs), I have been seeing a psychologist for 2years now, started my game studio in addition to my job, so overall I got everything on track.

Last year (march 2023) I broke up with my ex, we were together on/off for 1 year, and it wrecked me emotionally. I only got back on the app in December 2023 (I must open it on average once every 2 weeks), I can’t say I’m back on the dating scene either as I’ve never been a huge fan of flirting in bars or while I am out; When I am with friends, my mindset is “I’m with my friends, I dedicate 100% of my attention to them”. If you don’t have a sign, lights, and sirens to indicate you find me cute or wish something more, then you’re simply a friendly stranger in my eyes.

I don’t tend to stress while I am on a date, I take it as meeting someone new who’s got a different view of the world and I wanna learn what it is, I initiate light physical touch when appropriate and if it’s not reciprocated I stop, I don’t pretend to be the perfect date I do trip a lot but overall I try to make the experience as enjoyable as possible. The stress comes after (I shouldn’t have said that, you touched her arm you look like a perv, you’ll never get a 2nd date with her, etc…).

A few weeks ago I went on a date with someone I used to jog with (I was part of a running group but I switched to biking), after seeing her on the app we matched and started talking, the date went really well with the promise of doing something soon, but she got sick. My first instinct was not to think she’s lying or anything but more “She is not gonna be interested anymore, I’ve wasted her time, I should move on” even though the date lasted for 6h+, texts are still exchanged albeit at a slower pace but her answers are detailed and include a way to keep the convo going.

So how do I overcome this fear without resorting to the nuclear option of disappearing altogether and just giving up after the 1st date?

A Lonely Lost Lover

This, L3, is what we in the dating advice biz call “snatching defeat from the jaws of victory”.

It really doesn’t take much to see what the issue is: you’re overthinking things and missing the obvious because you’re focused on the past. Your anxiety and worry is spinning up and now you’re going over the date like coach of the 49ers going over the Chief’s performance pre and post T-swift entering the chat. The thing is: doing this isn’t actually going to help; it’s mostly going to hurt.

The problem when you get deep into the post-date analysis paralysis is that you end up so focused on what you did “wrong” that you end up creating scenarios for yourself where it couldn’t possibly had gone right and you convince yourself that anything that isn’t “OMG let’s get married tomorrow!!” is a negative outcome… and that you somehow caused this. And honestly, most of the time, that’s not actually the case.

When the anxiety weasels start to bounce around, it gets very easy to forget that other people have agency and feelings of their own, as well a life that doesn’t necessarily revolve around you. The cold and hard truth is that a LOT of first dates don’t result in second dates – especially when you’re meeting people off dating apps. This isn’t because anyone did anything wrong, but simply because there wasn’t the necessary x-factor for there to be interest in a second date. It’s very hard to suss out compatibility over apps, over text or even over video chat. There’s entirely too many factors that determine attraction and compatibility that can only be detected in person. As a result, you can end up with matches that seem amazing on paper, but have all the spark of a pair of damp cotton balls rubbing up on one another. That’s nobody’s fault; there’s literally nothing that you (or they) could have done. It was just “nope, not right for each other”, and thinking that you fucked up somehow is like blaming yourself because you couldn’t get a milkshake at Home Depot.

The thing is, screw ups and mistakes that ruined the mood or killed any attraction tend to not be subtle. If/when you did do something that killed the chances, it’s usually pretty obvious and you can feel the mood shift pretty quickly and significantly. Yes, it’s entirely possible that you missed something, but most of the time it’s easy to point to the moment where things took a turn for the “oh look I gotta go home and shave my cat”.

Now this isn’t to say that you can’t mess up or that things can’t have been doomed from the jump. But in those cases, the ones where someone is disappointed right from the beginning – if, f’rex you took her to McDonalds when she was expecting/wanting Le Cote Basque, she’s a sludge-metal fan and you took her to The Magic Flute – is a matter of different expectations, priorities and incompatibilities. You and your date having different expectations or lifestyles is, likewise, not a fuck up on your part, it’s just a mismatch. That’s all.

The second thing is: sometimes life gets in the way, but that doesn’t mean that you failed or fucked up. I’ve had dates where I thought things went well and then suddenly it was radio silence and I was convinced that I messed up. Turns out no, she was in the hospital for pancreatitis or dealing with plumbing exploding and flooding her house and we went out on another date after things settled down. That wasn’t a screw up, that was just bad luck. Again, nobody’s fault and also not necessarily something that couldn’t be recovered from.

In your case, the fact that your date got sick and couldn’t go out with you again soon doesn’t mean that things are doomed and it doesn’t mean that she’s going to forget you or the good time you two clearly had on your date.

This is one of those times when people misunderstand ideas of things like emotional momentum. When you’re talking with someone you’ve met on a cold approach or matched with on a dating app, you’re a stranger and, to a certain extent, not a person. You’re a possibility, and that connection is fairly tenuous. It’s not that difficult for the interest to start to fizzle without reinforcement because there’s really no foundation to it. Even on an in-person cold approach, it’s pretty easy to lose interest for an assortment of reasons that have nothing to do with you. The venue may have been loud and chaotic, they may have talked to a LOT of people, or they may have been in a different mood in the venue than they were at home the next day. That doesn’t make it your fault if they do; it just means that there’s less there to really anchor interest or excitement to.

It’s different when you’ve actually met up and gone out on a date. Now there’s actual material to work with, things to point to and say “yeah, this was a good time” or “I’m willing to go on another date and see…” Women don’t have the memories of goldfish after all. And quite frankly, you’re not the only person who worries about that lack of interest. Women also worry that if things get in the way of scheduling another date, you’re going to lose interest. If you can still be interested after two weeks when they couldn’t meet up, the odds are that they will be too. Attraction isn’t that fragile; if someone’s actually interested in you, then they’re not gonna lose that in the blink of an eye.

And if they do, that’s usually a sign there wasn’t much there to start with. But that’s ok; you want to date someone who’s excited to see you again, not someone who could take or leave it.

This, incidentally, is why I’m not a fan of letting things drag on after you’ve matched. Yes, it’s good to give your matches time to feel comfortable with meeting up in person, but the point of online dating is to date. That means meeting up and going on dates, not talking for weeks or (in some cases, months) until you feel 100% sure she’ll say yes if you propose a date. Taking that long means that she’s more likely to end up on a date with someone else. After all, she can’t go on a date you didn’t ask her on.

This is also why I’m a believer in a pre-date date, where you meet up for coffee or ice cream for 15 minutes or so and decide if there’s enough in-person chemistry to go on a proper date. It’s a smaller ask and easier to say yes to than rolling the dice on several hours with someone you may or may not like hanging out with.

Point being: sometimes you gotta take the W and realize that not everything means that you fucked up or that you failed, nor should you just jet when things get slightly inconvenient or your anxiety fires up. Otherwise you’re going to end up missing out on a lot of awesome dates and awesome people for no reason.

If you like this person, and she likes you, and the two of you had a good date with the promise of another? Don’t just abandon ship because the brain weasels went to town. Your anxiety will always find reasons why you were fucked before you started; that doesn’t mean that they’re real. Sometimes you’re reading too much into nothing. Sometimes your anxiety is just making shit up out of absolutely nothing. That’s why we call it anxiety.

What you shouldn’t do is be waiting with sandwiches by your laptop for when she texts or hits you up on WhatsApp. One date, even a really good one, isn’t a reason to lock yourself onto one person. You should be going out, talking to more people, messaging people on dating apps and generally continuing to just live your life. A date isn’t a binding agreement, nor is it a commitment to anything except possibly another date.

When she’s feeling better and wants another date, then you two can and should go on another date. But on the occasions when it really is a first date to nowhere, not putting all your attention and energy on one person who you saw one time is a hell of a lot healthier than sitting around stewing and trying to go over the date like it’s the Zapruder film. I promise you, the vast majority of the time, everything is as it seems on the surface.

You can’t critical path your way through dating. It’s messy, frequently chaotic and everybody trips over their own two feet, tongues and junk all the time and honestly that should make us all feel better. If we can all embrace the mess of the human condition, it becomes a lot easier to give ourselves the grace that we frequently give others and we can all learn to relax and just be in the moment.

Good luck.

Hi, I’ve got a bit of dilemma

I’ve had a crush on this guy for a while now but a few months ago I found out him and a girl I know from college were sleeping together. At the time it didn’t really bother me too much, but now it’s been months later and my attraction towards him has progressed

They don’t sleep with each other anymore, but I guess my question is, if something was to happen between us, would it be wrong to pursue it? The girl didn’t know I crushed on him, and we aren’t close and don’t speak or anything outside of college, but I get anxious about making people uncomfortable and we’re not on a level where I could ask her if it she would be okay with it.

It’s been weighing on my mind massively and I feel like a bad person for having these feelings but I’m really attracted to him and I can tell he feels the same way but I don’t want any trouble what do I do?

If you could give me some advice that would be really appreciated.

Who’s Turn Is It?

Alright, it’s story time, WTIT. I know this is going to sound like a digression, but stick with me for a second. I promise, this is going to make sense for your situation.

Back in the Before Times, the Long Long Ago, I started dating Dr. Mrs. The NerdLove. As was the cringey custom at the time we actually made it “Facebook Official”; that is, did the “relationship status” change that ends up as a post on your timeline. When we did, a mutual friend of ours, who I used to date waaaaay back when, was put out. Apparently she was upset that we didn’t tell her in advance or get clearance from her to start dating.

This made precisely zero sense to either of us, seeing as my ex and I had been broken up for more than a decade but also what business was it of hers what either of us do? So we both shrugged our shoulders, said “whoops” and just moved on.

I mention this because the absurdity of the idea that either of us should get “permission” or check in with my ex before we start dating is pretty self-evident. People can be in their feels about something, but that doesn’t actually obligate other people to do something about it.

Here’s the thing: people aren’t the next turn at the pool table or something being offered on a Buy Nothing group. You don’t get to call “dibs” on a person and if you’re not in a relationship with them, you don’t get a say over who they date or sleep with. People can feel how they want about it, but that’s a them problem, not a you problem.

If you’re friends with someone and you know they have strong feelings about someone you’re about to date or hook up with, then sure, you might want to give them a heads up so that they can at least brace themselves and not get hit out of the blue. It’s considerate, but not mandatory; it’s not as though you’ve committed a horrible sin if you don’t. However, please notice that I said “give them a heads up”, not “ask their permission” The fact that they are having feelings about it doesn’t mean that they get a vote or a veto in your business or the other person’s.

But in your case, you don’t seem to have any relationship with this other person outside of “former classmates”. You’re not obligated to clear things with friends, never mind people who are, at best, nodding acquaintances. It’s not your responsibility to manage other people’s feelings for them, nor is it your duty to forgo a relationship because someone else might have a sad about it. 

If they have a problem with it… well, they can have a problem with it. But it’s not your problem. It’s not even her ex’s. It’s hers, and she can put on her big-girl pants and deal with it. If she tries to make it your problem… well that’s what “mute” and “block” functions are for. 

You like this guy. He apparently likes you. That’s all that really matters here. You two are the only people in this equation who get a vote in this. So go ask him out and see what happens. You have my blessing… not that you need it.

Good luck.