Should I try again in January?

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I've been getting back into dating after a breakup over the summer. That relationship lasted more than two years.

I'm back on the apps, which is where I have almost all of my prior experience with dating. I met my ex on an app after five years of dates that went nowhere, so I know it can take time and patience.

I've had a lot of lackluster interactions with guys over the past few months – until one man in November. We hit it off immediately. Great conversation, good chemistry via text, some shared interests (which is important to me after my last relationship). He was clear about his interest in me, which was a refreshing change of pace. Right as we were planning to meet, he got some terrible news about a friend's death. We discussed how he was feeling, but still ended up going for a date. Chemistry was there in person, even with the heaviness of the news, and he made it clear he wanted to see me again (which also happened). This was the weekend before Thanksgiving.

His level of communication tapered off over Thanksgiving week, which I chalked up to the holiday and the news about his friend. I reached out on a Sunday to check in on how he was feeling/doing. He shared that he was struggling more than he thought, and told me he needed to take a step back from dating for a bit. He asked if he could get back in touch with me after the new year. I said sure, and I respected his self-awareness. He thanked me for being understanding and apologized for being "difficult" – but I told him that knowing his own needs and communicating them is not being difficult at all.

I'm still very interested in seeing him again. I'm hopeful he will reach out, but I'm also not holding my breath waiting for him. Given a lot of our conversations (a lot of openness from both of us about mental health and other baggage), I also know he's an anxious person, and part of me worries that he won't try to reconnect because he'll think he's been too "difficult" or that I'm not interested any longer because of the time he took in stepping away. I want to respect his boundary and give him the chance to reach out when he's ready, but part of me is telling me to reach out mid or late January if I haven't heard from him (and if nothing has developed with anyone else I want to pursue). I can see pros and cons to either approach, but I'm just hoping to get a little more perspective from people outside of my immediate circle because this is such a unique situation.

– Hopeful, But Not Holding Out Hope

If you haven't heard from him a few weeks into January, I don't see any harm in reaching out. But I wouldn't make any big requests. No "How are you?" questions that are too complicated to answer.

I'd invite him to something fun and easy, like a movie. You could say, "Hey there, I’m distracting myself with a thriller today. Want to hang out and eat popcorn for a few hours?" Low stakes. Just fun. It's an empathetic path to hanging out, because it's easy for him to say no without making some big statement.

If he tuns you down, assume the ball is in his court to follow up with another easy idea. If he doesn't, that's that.

If he makes it difficult to get together for all of January, that is the answer. It sounds like you're looking for a significant relationship, and he might not be up for that right now. It would be nice for you to start something that doesn't require a ton of work – or a chase. I know that connections like this are rare, but you need to be with someone who shows up for you. If he can't do that, move on.

Try to focus on your other dates, if you have any over the next two weeks. Give these people a real chance, even if you're holding out some hope for this other person. You can multitask.

– Meredith

Readers? Reach out? Let him decide?