Should I ask to see him again?

[Anonymous]

Hello! I have been chatting with this guy for two months. We have met for icecream once. I asked him to hangout then. A bit later he asked me to hangout again but there was a cyclone so we couldn’t. After the weather event we tried to organise another meet up but we had conflicting schedules due to uni and work. I have a much more free schedule but his is jam packed with work and uni. Should I ask him to hangout again or wait till he asks me? We are both very awkward and I haven’t dated in five years so I’m not sure how it works anymore. Thanks!

[Oliverlogan263]

Ahh girl, that's a tough one. I can totally see why you're feeling a little unsure about what to do here. Navigating the dating world can be super awkward, especially after a long break.

On one hand, there's nothing wrong with you taking the initiative and asking him out again. The fact that you've both made attempts in the past shows there's definitely interest there. Plus, if your schedule is more open, it could make it easier to find a time that works for both of you.

The only thing I'd caution is that you don't want to come on too strong or make him feel pressured. Dudes can sometimes get a little freaked out if a girl is too forward, you know? So maybe try something casual, like "Hey, I was thinking we could grab dinner this weekend if you're free. Let me know what works best for you!"

That way, you're putting the ball in his court a bit, but still making it clear you'd like to see him again. And if he's interested, he'll probably jump at the chance.

The other option is to just wait it out and see if he reaches out again. That might take some of the pressure off you, and show that he's genuinely making an effort to make plans. But there's always a risk that he could get busy or lose momentum, and then nothing ends up happening.

Ultimately, I think it comes down to how much you're feeling this guy. If you're really into him and excited about the possibility, go for it and ask him out. But if you're on the fence or worried about coming on too strong, you could wait and see if he initiates something first.

Either way, don't stress too much about it, okay? The right move will reveal itself. Just be true to how you're feeling, and don't be afraid to put yourself out there a little. You got this, girl!

[FoxyFatale]

I’d say go for it and ask him! It’s been a while, and since you’ve both been super busy, a casual “Hey, we should hang out again soon” could be a good way to see where he’s at. Don’t overthink it. It’ll show you’re still interested, and if he’s into it, he’ll make time!