Estimated reading time: 15 minutes
Hey Doc,
I’ve been reading your column for a while and I appreciate your no-bullshit approach. I’m going to try to do the same here.
I’m in my early 30s and I met a woman — I’ll call her K — at a martial arts class a few months ago. We started talking consistently after sessions, usually a quick chat by our cars. My intention was always just friendship, with an openness to something more if the timing ever worked out. I wasn’t in a rush because I’m deep in a job search and I thought she might be seeing someone at the dojo.
That guy turned out to be mostly out of the picture. She mentioned a couple of times that he was “kind of a loss” to her, and last I heard from her, he has a new job and a new girlfriend. So, things felt low-stakes.
Over the past few months, things escalated naturally. I asked if I could join her for coffee and she said yes, we talked for an hour. When I mentioned I’d be near her workplace to meet a friend, she suggested I stop by and took a break from work to hang out, again for about an hour. She gave me a nickname, little touches on the arm, that kind of thing. Then a party came up through a mutual friend. She suggested I go, later texted me that she’d be going too, and showed up with a date. I was outside my comfort zone and handled it awkwardly, but we kept talking after class like normal.
A week or so later I asked if she wanted to hang out sometime outside of when we had been (randomly on weekends). Not a date, just to hang out. She said sure pretty quickly and even suggested dinner after class. I told her I didn’t want to get in the way of anything with the new guy; she kind of laughed and didn’t really answer.
I dropped the ball on following up — three days, between job searching and nerves. I eventually sent her three restaurant options. She replied at 11 PM to say she was really sick but didn’t want to leave me hanging, and that dinner after class wouldn’t work because of her early mornings. I didn’t see it till the next morning.
I wrote back the next day after talking with a friend. My friend suggested I write that I hoped she felt better, offered a raincheck, suggested a time when we didn’t have class, and said I could follow up next week or whenever I saw her. She read it and never replied.
The next time I saw her at class, things were different. Since before we started talking, she’d stand on the same side of the room as me. This time she went over to the other side of the room without making eye contact. I went over, said hi, asked how she was feeling. She said it was just a cold. She agreed to catch up after class. After class I waited by my car (which was near hers) without hovering, just packing up. When she came out it looked like she rolled her eyes, got in her car with zero eye contact, and drove off immediately, which is unusual for her.
My friends tell me I did nothing wrong and that her behavior is weird. And I don’t think that’s totally fair. She is angry at me, and something I did led to that. I feel bad about that and would love to clear it up with her. But I also don’t think the way she handled the situation is right.
I haven’t seen her since. My plan is to give her space, be cordial if we cross paths, and not make it weird. I don’t think I’d pursue anything romantically with her after this, but I did genuinely enjoy her company and I’d like to not have this be a source of ongoing tension at the dojo.
What did I actually do wrong here? And is there anything I can do at this point, or do I just let it go?
– Friendly Fire
This sounds pretty clear-cut to me, FF. Between a whole lot of unfounded assumptions and some avoidable mistakes, you ended up sending the message that K is a low priority for you and your interest in being her friend and hanging out is conditional on whether you think she’s single or not.
I’m going to leave off whether she was sending flirting signals or not – it sounds like she was, but this is why having context is important – and focus instead on your side of things. You were hesitant to get to know her at first because you thought she might be seeing someone, but then you seemed to be escalating the amount of time you saw her when you found out that her boyfriend “was mostly out of the picture”. Then, at the party, she comes with a plus-one. Now, maybe this was a date. Maybe this was a friend. I don’t know, you don’t say, and I suspect you never really got confirmation one way or the other… but you say you handled it awkwardly. I wish you’d said more about this because there’s a strong likelihood that this set the stage for everything that happened afterwards.
A week later, you ask to hang out, she suggests dinner and you go out of your way to mention the guy you saw her with. Then, having gotten what, admittedly, is an unclear response, you just straight bail for three days, before making a really low-effort attempt at arranging the date.
She responds, clearly annoyed and saying “you know what, never mind”, and your reply was… well, honestly, I could see it coming off as not reading the situation correctly. I think you missed that she was upset at you and telling you not to bother, because you were acting like you weren’t interested and she was a low priority at best.
Since then, things have been strained, with no sign of this abating. And, based strictly on what you’ve written here… I’m not entirely surprised. There are a number of ways that you messed up here, my guy. I can understand the awkward of seeing her show up to the party with someone – been there, done that, back in the day – but that probably set a tone. So too did the mentioning her maybe-maybe-not boyfriend when there was no real reason to. And then there’s the fact that you don’t say whether you offered up an apology for the way you went radio silent. If you didn’t, then that definitely ain’t helping matters.
Nor, for that matter, has keeping your distance. If she – and I’m speculating here – thinks that you were trying to Nice GuyTM her, then your behavior has been carrying a pretty clear message, one that you may not have been intending to send, but one you’re sending regardless.
There are a lot of unforced errors going on here, but most of them weren’t fatal in and of themselves; it’s the accumulation that’s the problem. The two that were the most egregious were how you handled her inviting you on a date and how you’ve handled things since.
The whole situation around the date is… not good. Bringing up the guy you saw her with – especially about “not getting in the way of anything” – was really unnecessary and more than a little presumptive. You didn’t know if she was dating this guy or not, what kind of relationship they had, and it wasn’t relevant to the two of you getting dinner. Even if she and this guy were dating and had gone exclusive already was beside the point; people can and do go out to dinner with their friends – even if they’re in a relationship. Hell, even if they’re in a relationship and they’re going to dinner with someone they might plausibly sleep with. Bringing it up was an awkward non-sequitur at best and it set the stage for everything that’s followed.
I understand what you were going for here – you were trying to feel out whether this was a date date and whether she was single or not. But whether it was and whether she was, this wasn’t the way to handle it. First, it’s not on you to try to presume whether you’re “getting in anybody’s way”; she’s a grown-ass woman and can handle her own affairs – both literally and metaphorically. It gives the vibe of “wait, I can’t associate with you, another guy put their stamp on you first”, which isn’t something you want to convey, period. But when combined with how you blanked her on the date for three days with no word and the way you’ve behaved since? That’s not great, and I wouldn’t be shocked at some of the conclusions she may have drawn from all this.
Most of this could’ve been handled if you’d made some better choices. Not going for three days without making plans and no contact was a big one. Another would’ve been to not bring up Schrodinger’s Boyfriend. I think she was asking you for a proper date, but if you were unsure, the best thing you could’ve done would be to say something along the lines of “Just so I’m clear, are we talking about a date?” instead. If it wasn’t a date, or there was someone else in the mix, she would’ve told you, and you would be dealing with a lot less confusion and speculation.
But here’s the thing: have you noticed how I’ve said I’m guessing and speculating at how K is feeling or thinking or what she intended? That’s because I am saying I don’t know what’s going on in her head.
That’s important, because literally all of these could’ve been avoided, if you’d done something you hadn’t done and, as near as I can tell, still haven’t done: you haven’t talked to K. You’ve talked to other people, you’ve asked other folks what they think and got their advice and opinions, you’ve even written to ask me, a complete stranger. But it doesn’t sound you’ve talked to the one person who could give you some definitive answers: K.
K is the person who can tell you whether she’s mad or not, so if you want to figure out how to defuse any potential tensions at the dojo, she’s the person you’re going to have to talk to. I’d strongly recommend starting with an apology for how you’d been acting and for the fact that it’s overdue. I would even suggest you say that you wanted to give her some space, but you realized that is probably sending the wrong message and you’re sorry for not saying something sooner. Do not use the passive voice in these apologies; you’re not sorry she was offended, you’re sorry you offended or upset her. You can mention that you were nervous and unsure, but it’s important to be clear that these are explanations, not excuses. Tell her you really enjoy her company and want to be friends, but you understand if that’s not something she wants any longer. And then, you wait.
Maybe the two of you will be able to shake this off and be friends. Maybe she will tell you to take a flying fuck at a rolling donut. Maybe she will tell you what you did, specifically, that pissed her off. Maybe she’s not pissed at all and she’s got her own shit going on that has nothing to do with you. You don’t know. I don’t either. She does, and at this point, your guessing, assuming and doing anything other than straight-up asking will only compound things further.
Will you be able to resolve things with her? I have no idea. But whether you do or you don’t, you should take this as guidance for the future: use your words. If you’re not sure about something, ask them… before you end up wondering just how you fucked things up.
Good luck.
Hi Doc,
I reached out to you a few years ago about my struggles with dating. I’ll keep things vague, but it was one of those “I’m a good person, so why can’t I find a date?” letters. I remember reading your reply and the discussion back then, and revisiting the letter recently was painful. It’s hard to see that I’m still in the same place.
I’m still here, still trying, but still very much alone.
I continue to put myself out there to try and connect with people. Over time, I’ve formed one fairly close friendship and built some lighter connections with others. However, I still spend birthdays, holidays, and most meaningful moments on my own. I haven’t had the stability to make a bigger change, like relocating. I’m still consistent with things like the gym and therapy, but I’m not really seeing the fruits of my labour. I do interact with women, but it’s very clear they don’t see me in a romantic way.
It feels like I’m just drifting…like I’m stuck and not moving forward. I’ve started a temporary job where everyone else seems settled; they’re married, have families, and share close bonds with each other. It’s a tight-knit environment, and in contrast, I feel like an outsider, just passing through, on my own.
I remember embarking on my self-improvement journey a decade ago, absolutely obsessed with working out why I was struggling, and I feel like I am not one step closer to experiencing any form of romance. My new friend absolutely insists I’m a catch, that people (especially women) like me, and that I’m one of the best men she’s ever known.
If that’s true, I can’t help wondering why my reality looks so different. I’m half-way through another decade, and still trying to find the answers. At what point do I question whether I’m missing something fundamental about myself, or doing something wrong without realising it? I’m tired of feeling like I’m on the outside looking in, and I don’t know what else to change, or if there even is anything left to change at all.
What Am I Still Missing?
Can I ask you something, WAISM? Among the friends you currently have, how many did you actively befriend and how many were the ones who brought you in? I ask because I’m going to be blunt here: I think the problem you’re having is that you’re not actually putting yourself out there, not really. Putting yourself out there doesn’t mean just placing yourself in physical proximity of others, it means that you have to communicate your interest in getting to know folks – whether as potential friends or potential dates.
Moreover, I think you’re starting from an assumption that you’ve been pre-rejected and you have to work yourself up to being seen as neutral before you can get anywhere. And even then, it sounds to me like you’re working from assumptions and not actual facts.
This is the part that leaps out at me, and it’s something I see a lot in letters like yours: “where everyone else seems settled; they’re married, have families, and share close bonds with each other. It’s a tight-knit environment, and in contrast, I feel like an outsider…”
The key word here is “seems”, and it’s doing a lot of heavy lifting, because I’m willing to bet cash money that you haven’t actually tried to connect with them. This is, quite frankly, distressingly common to see in guys (and it’s mostly guys) in your situation – the assumption that all social circles are closed with no new openings or roles to be filled; they’ll keep your application on file and contact you if anything opens up. It’s that precise attitude that infects your interactions with other people – the presumption that these social circles are closed and exclusionary and there is no room to be found to bring a new person in.
Now I get how an established group can feel intimidating, especially to someone who’s new and doesn’t know anyone yet. They have a lot of shared experiences and history, references and inside jokes and who knows what else. But that doesn’t mean that you can’t become part of the circle. You aren’t going to be expected to pass a test. You didn’t miss the two-week window where people were grouping up and then no other people would be allowed entry. And really, the odds that this group is going to look at someone new and say “sorry, you’re surplus to requirements” are low. Most friend groups aren’t so exclusionary that they never let anyone else in; in my experience, folks tend to be cool with making new friends and bringing them in. The only real bar to entry is “is this person someone we enjoy hanging out with?” If the answer is yes, then it’s all done and dusted.
I suspect that this attitude and behavior applies when you are interacting with women too; it sounds like those interactions are just that: interactions. Not attempts to make friends, or bring things closer, just assumptions that you’ve failed before you even stepped up to take your shot. And that’s not going to help you make friends or find dates. You can’t just stick a toe out the door and hope that everyone else will take you the rest of the way, and you have to be willing to be proactive about connecting with people. That means, among other things, letting go of the idea that you’re pre-rejected or that these ties are so close-knit that there’s simply no way that someone cool couldn’t ever be added in.
As I’ve said before, it’s one thing to trust your gut and your read on a situation, but that first requires that your gut is trustworthy and your read is accurate. And I am betting good money that yours isn’t. Sometimes you have to be willing to accept that maybe you’re not the clear-eyed reader of The Signs, especially when you are coming to that reading from a place where you think your presence is something you need to apologize for.
And not to put too fine a point on it, but every insider starts as an outsider; they just don’t sit out there staring in and hoping that maybe someone notices and adopts them in.
If you want to make progress, you’re going to have to actually put yourself out there and be much more motivated about meeting people. This means taking steps like “introducing yourself”, “asking if you can sit with them at lunch”, “make conversation that goes beyond what’s necessary for work” and occasionally “invite them to do stuff”. If most of your interactions with people involves the bare minimum of small talk and no other indication that you might actually like to have a personal relationship – like showing an interest in who they are when they’re not on the clock, talking to them about more than work and occasionally making the initial overtures of friendship – then you’re going to be stuck in the same rut.
It also means – especially if you’re trying to make friends – not giving up after the first “I’d love to but I can’t.” Sometimes that’s a “no, not ever”, but other times, it’s a “maybe a bit too soon, try again later”, and you simply haven’t had enough time to reach the stage of socializing after work. Or it could even be a genuine “I would love to but I can’t”, not a polite refusal; sometimes people really are busy or have other plans but would’ve said yes otherwise.
Good luck.
