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Ask Anna: I said yes to a second date and now I'm dreading it

Anna Pulley, Tribune News Service on

Published in Dating Advice

Dear Anna,

I went on a date with a couple recently. I’ve been a unicorn before, so I’m not completely new to the experience, but I wasn’t sure whether it was something I still wanted — and, honestly, I’m still not sure. The date itself was fine! We had fun, and afterward I wanted to see them again, so told them as much. But now I’m looking at my calendar and feeling overwhelmed. Instead of excitement, I’m feeling a lot of dread and obligation around fitting this date in. So now I’m wondering: Is the dread telling me I’m actually not that into them and should let them go? Or am I just genuinely overloaded right now? Would it be weird to tell them my schedule is a mess and ask if I can check back in next month? — Overbooked Unicorn, Trying

Dear OUT,

Well. Dread and obligation are definitely feelings to listen to. Though neither are necessarily a verdict. Sometimes “Ugh, I don’t want to go on this date” means I don’t want to go on this date.

But sometimes it means I have 47 things on my calendar and the idea of adding one more to the pile makes me want to throw myself into the sea.

Those are different camps. Let’s tease them apart.

First, imagine that tomorrow morning a magical entity — let’s say a supernatural sloth because why not — cleared your whole calendar. No errands, no deadlines, your toilet paper no longer needs replenishing, and even the cat doesn’t need you. You suddenly have a completely free evening.

How would you feel about getting drinks with these two? Excited? Curious? Mildly interested? Neutral? Relieved that you don’t have to?

If that thought experiment doesn’t clear things up, then ask yourself a slightly different question: If they texted right now and said, “Actually, we’re going to have to cancel,” what would you feel? Disappointed? An enormous, involuntary THANK GOD? Pay attention to the first emotional reaction before you start explaining it away.

There’s also a third possibility worth naming: Some of that dread might be about the logistics and emotional math that come with dating a couple specifically. Whose feelings you’re managing, how investment lines up across three people, what happens if you click with one of them more than the other. That’s a real and separate thing from “am I into this person,” and it’s worth asking yourself, if you haven’t already.

I’d also separate two questions that are getting tangled together here: Do I want to see these people again? and Do I want to pursue being a unicorn again? You don’t have to know the answer to the second question yet.

 

Maybe you enjoyed them and are curious enough to have another drink. That’s enough. A second date doesn’t constitute a binding contract to join their polycule, become their regular third, or even have sex with them once.

And, of course, if you really can’t tell if what you’re feeling is life overwhelm or just overwhelming meh, you can defer your answer.

Something like: Hey! I know I said I wanted to see you both again, and I meant it, but I’m realizing my schedule is completely bananas right now, and I don’t think I can give drinks the attention I’d like to. Can we check back in next month when things have calmed down?

That’s honest without being too in-the-weeds about it. And don’t promise a future date if you’re secretly hoping they’ll forget about you. If you send that message, actually check back in.

If you get to next month and the thought still fills you with dread, there’s your answer.

And give yourself permission for their answer to be no, too. They might not want to wait a month, or they might hear the deferral as a soft pass — and either reaction is fair. You’re not responsible for managing that outcome perfectly.

There’s another thing I’d consider: Are you feeling overwhelmed by them, or by the idea of dating at all right now? If your entire calendar feels like an endless series of obligations and even things you normally enjoy are starting to feel like chores, this may not be a unicorn problem. It may simply be a bandwidth problem.

That was a lot of questions to think about, wasn’t it! In any case, give yourself permission to remove the deadline. Make some space. See what remains when the obligation falls away.

If curiosity survives the calendar, follow it. If only guilt survives, as Supernatural Sloth would say, let them go.


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