We've been in the same friend group for years but really haven't spent much alone time together at all. I was told he's had a thing for me for a while now, and since I just moved back to my hometown he's been pursuing it a bit more actively. Hasn't full on asked me out yet, but I can tell he's working his way up to it.
So I'm faced with a dilemma. I like him well enough. He's a good guy. He's pretty darn attractive. But I don't know.. the few times we've been alone together, we had a hard time finding stuff to talk about. I'm not sure we have much in common. He's really fun to hang out with in a group, but when it's just us it's, I don't know, less comfortable? Slightly awkward? Struggling to keep the conversation going? And the risk is high because we're in the same friend group. Our mutual friends are married to each other. If we started dating and it didn't go well, I worry it'd make hanging out weird.
Feel free to weigh in. Give me all your thoughts. I want to think this through from every angle. On the one hand, I don't want to turn down a perfectly decent guy. On the other hand, I don't want our friend group to turn awkward (I'm distinctly bad at dating lol, I just get nervous and clam up). There's a million ways it could go wrong and only a tiny chance it'll be amazing.
Most Helpful Guy
If you have had trouble getting along one on one in the past, it will be evermore difficult if you're on a 'date', and chances are your friends are waiting to hear about it from one or both of you.
There will be more pressure now that previously. And it didn't work well previously, as you describe.
I'd explore what he's thinking while you're still going out in a group, and also ask the other people what they think of him. Stay distant for now until you get reassuring answers to your questions.1
Most Helpful Girl
I did that and when we broke up after 3 years, I lost many of my friends. Now, every situation is different, but I wouldn't do it again.0