How do I move from the longest talking stage of my life?

I don’t really know how it’s making me feel anymore. 

Here’s The Thing is an advice column/newsletter where I mostly beg people to either stop dating someone or to ask their crush out. Or I talk about weird things that came to my mind that no one is paying me to write about. I can never decide if I should capitalize the “the” in Here’s The Thing or not; apologies on lack of consistency. 

You can submit your own question—or yell at me about how I’m wrong—by emailing me at


I’ve been talking to this guy pretty much every day for the past year, ever since the pandemic began. He’s a friend of a friend who I’d only met once before the pandemic started — we’d had a friendly chat and followed each other on social media, but that was that until the pandemic hit. We began talking about a month after first lockdown started — we were DMing about a show we were both watching, and it just continued from there. These things always tend to just fizzle out, but somehow, it kept going. We were messaging loads pretty much every single day, and at the time I didn’t think much of it, because he’d moved back in with his family out of the city where we both lived and he didn’t have a timeframe for when he might be moving back, so it was a fun, low pressure kind of situation which took my mind off the lockdown. Inevitably, though, I began to think about what the vibe might be — if there might be something more than friendship there. I hadn’t noticed any kind of spark when we had met for the first time, and it’s not that I was developing feelings, exactly, but I was kinda curious to see if there might be something there. I never mentioned it though, much to the chagrin of my friends, and neither did he — why would we when we weren’t in the same city and we were still in lockdown? 

This went on for about five months (yes, I’m a clown) and finally, he mentioned that he might be coming down to the city for a couple of days. I got annoyed because he didn’t message until he was actually in town, and I felt like his request to meet up was kinda offhand and I didn’t appreciate that, but I also felt silly for being annoyed. We did end up meeting up though, and it was really nice. We got drinks and spent about six hours together, just talking. I felt like there was a romantic energy there, but neither of us made a move. A couple of days later, spurred on by alcohol and a friend, I messaged to ask if he thought there was a more-than-friends vibe. He eventually replied that he thought there was, but that he didn’t know if he could do anything about it considering his living situation at the moment. So, we kept on messaging at the same intensity as ever, and have been up until now. 

I’m in my mid 20s and basically haven’t dated for the last three years, since a big break up. I feel really fine about that break up now, but I didn’t feel ready to date for about a year after that relationship (and a subsequent rebound relationship that got way too serious too quickly and freaked me out). I’ve also always really really struggled with body image and dysmorphia — I find it impossible to think that anyone would find me attractive and that has been pretty bad for the last couple of years. I feel a little more confident now, but I’m still scared of rejection (clearly!) and of putting myself out there. This protracted talking stage with this guy has me feeling weird about myself now — I feel like I kinda have to keep talking to him and if I let it drop off then I’ll ruin my shot at maybe being able to date him if/when he moves back to the city, but I also feel kind of deranged and desperate for feeling that way, and I hate that I am just sitting on my ass waiting for him, in some respects! I want to go out and date other people, but I feel an odd sense of loyalty to him (which I’m sure he doesn’t feel about me) and I’m also shit-scared of doing so. I don’t know if I should peel off from talking to him (a friend said I should continue as long as I felt like it was making me happy and not sad) but I don’t really know how it’s making me feel anymore. 

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Howdy, love! You’ve come to the right place: I love weighing in on crushes and almost-somethings.

I don’t really know what to tell you because you don’t know how you feel and until you know how you feel nothing I say really matters because, get this: there is no right choice here. There’s no control group for life. You can’t run the test one way (continuing to talk to him) and see how it goes, and then run it another way (breaking things off with him) and then choose which one you prefer. You just have to go forward. It’s a bit of bullshit, if you ask me.

My strongest recommendation for a thing you can do right now is to write your feelings down (even just writing the letter to me is a great start). Write down how you feel after you talk to him; write down what your best and worst case scenarios are; write down what you’re worried about, excited about and dreading. Even if you’re only taking your best guess at how you’re feeling, write it down. You can say, “I think I might be doing X because I feel like Y right now, but I’m not sure.”

And then, once you write it down, try your best to let go of thinking about it for the rest of the day or the hour or whatever period of time. The purpose of writing it down is twofold: 1) sometimes you find out what you’re thinking/feeling during writing. 2) writing will give you specific time set aside to think about this so you aren’t spending the whole day obsessing over it.

It’s really really really easy to fixate on situations like this, where it feels like there’s a right answer you can get to if you just think about it hard enough and where it feels like the stakes are very high (Either you could end up dating this person!! Or what if you break it off too soon and ruin your One Shot at Love!!) But I’m here to remind you that there is no right answer! There simply isn’t!

But also, the stakes aren’t going to Make or Break your life. This isn’t your one shot at dating, this isn’t the altar upon which you must sacrifice yourself. This isn’t the first or last person who wants to date/fuck/kiss you. Deciding what to do now, though it will of course have an effect to go with the cause, does not determine your entire future. You don’t have that much power. Please try your very hardest to remove some of this pressure from yourself. It’s not like the right answer is out there and you’re too foolish to know it. In the words of Natasha Bedingfield, “The rest is still unwritten.” I’m kind of joking, but seriously, nothing has happened yet. You don’t know what a future looks like with this guy at all; what if he moves in town and you go on a few more dates and you decide that you don’t like him? What if he doesn’t move back for some reason? What if you meet some guy named Anthony that everyone calls “Big Tony” that you fall in love with in the meantime? I don’t know! You don’t either!

I don’t think you’re a clown or a fool for having talked to a guy for this long. It’s lovely and nice to talk semi-flirtatiously to another human. How could that not be lovely? I don’t think you need to either hold out hope that he moves in town and you two fall for each other truly, madly and deeply and have a bunch of sex and babies (to mix up two Alan Rickman films), OR that you break up with him right now in order to go have a bunch of hot sex with randos in order to Prove Something. I don’t think you owe him any loyalty or exclusivity, but I also don’t think that it’s nuts of you to feel squidgy about dating multiple people. I personally think dating someone else or multiple people, if that’s available to you, sounds like a fabulous solution, but if you don’t like the idea of it, don’t force it!

Waiting to see what happens with someone, letting the chips fall where they may, is not always an act of desperation or weakness. (I also don’t think that acts of desperation or weakness are inherently bad, but that’s for another day and another letter). You can decide to see where this goes with him and not pursue anyone else simply because you’re enjoying this long talking stage and it not be about desperation. This can be—in fact, I strongly recommend that it is—a time for you to focus on yourself while he isn’t in town. This can be a time to really think about what you want out of a relationship so that when you get new information from this guy about what he’s looking for, you know if it lines up or not. This can be a time to work on friendships, hobbies, all the shit that makes up a life that isn’t romance. (I’m sure you’ve been doing a lot of that the past few years, but it’s never wrong to keep pouring more good Just For Me shit into your life).

That said, when/if he does move in town, it will be pretty easy to tell if he’s as into the idea of being together on a romantic level as you are, or if what he’s interested in isn’t what you’re interested in romantically. (Right now he seems hesitant, but for very very very normal reasons like not living in the same city). If he moves to your city and doesn’t make an effort or makes an effort that looks like letting you know he’s free last minute like he did with his “I’m in the city” plans, then you know he’s not serious about this and not worth your time.

The major point is this: you aren’t running out of time. This isn’t a game of musical chairs. Your only job is to explore the relationship as long as it feels like it’s nice. If you don’t feel like it’s nice or if you really can’t figure out if it’s making you any happier, then it’s probably time to let go of it. This season of life is pretty hard and lonely, you aren’t a fool or a clown for hanging on to things that make it less so. Not everything in this world is about moving on from things as quickly as possible, being efficient, not wasting time. You don’t get an award in heaven for having “wasted” the least amount of time with romantic partners that weren’t The One; I can promise you. I would—and often do!—argue that spending time getting to know a person, even if nothing comes of it is not a waste of time in the least.

So, give yourself a break. You don’t have to make any decisions now. Try your hardest not to close yourself off to other people/opportunities, but also don’t beat yourself up if you find yourself putting a lot of eggs in this basket. That’s ok! That’s life! We get attached to people and that’s kind of The Whole Point. If this doesn’t work out, I’m sure you’ll feel sad on some level, but you will survive it; I swear. Give yourself permission to not know the answer. Because you don’t! You can’t! There isn’t one!

You can submit your own question—or yell at me about how I’m wrong—by emailing me at