How long should I wait before contacting him again?

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I know there are no set rules, but still curious what people here think.

I messaged someone I'm interested in on a dating site of sorts. We exchanged several pleasant messages. I let him know I'd like to get to know him a bit, play 20 questions, that sort of thing, and eventually meet to see if we click in person. He let me know that he's getting over a relationship breakup (don't know how long term it was) & not really in the right headspace to do that right now, but would save my contact info for sometime a bit down the road.

How long should I wait before sending him any kind of a message? I don't want to message too soon and annoy him. I also don't want to wait too long, either. I know.. no set rules on timelines for these things. Obviously a day or two isn't long enough lol, but I'm just curious what you people here think might be an appropriate duration before messaging again to say hi or anything else.

I wouldn't message him again unless he send you a message, first. If you do, you'll only appear desperate. The ball is now in his court. You'll just have to wait and see if he knocks it back.

Very good point. Something I did think of, but wanted to hear advice from others.

I intend to leave the ball in his court & not message or email any time soon. However, if x-time passes w/o hearing a peep I think I'd shoot him a "hey what's up" kind of message. Trying to figure out what sort of time frame would be acceptable for that.. at the present moment, I'm thinking something like a couple of months.

I think he's trying to letting you down easy when he said he's not ready to meet anyone in person. So in this case waiting a couple of months seems appropriate.

Wait a good long while. A month.

Wait until you see something or experience something that he's talked about enjoying. Send him a message and say "I saw this and thought of you..."

If you then don't hear back. No more messages.

You could wait and contact him in a few days.. or you can contact me today

Its a possibility, but I really don't think so. I think he was being genuine when he said he wasn't in the headspace to chat (by pm) and get to know someone right now as he's getting over a breakup.

A guy truly "not looking to date anyone right now" likely wouldn't have a dating profile up in the first place. It's possible he's being truthful, however you at least need to acknowledge the possibility that it may be a soft rejection and not try to get your hopes up too much.

I said it's a dating site of sorts.. not exactly dating profiles on it for the most part. In general, it's used as a gay hookup site for casual sex vs. dating profiles. But there are some real & genuine guys on there.

I already acknowledged the possibility that it may be a soft rejection in my post above where I wrote "its a possibility." But the handful of messages we exchanged seemed genuine.. that and I asked him flat out of he was interested in chatting further, getting to know each other a bit, playing 20 questions - that sort of thing, and then meet sometime. He didn't say no, instead he let me know he's just getting back into flirting with guys but isn't in the headspace to get to know someone/meet etc due to still getting over a recent breakup.

Obviously I'm not going to hold my breath on this.. but I do hope I hear from him. There are a LOT of gay guys in this city, but so very few I'm actually interested in. Time will tell.