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
You need to find ways to be comfortable with each other. He is also probably nervous. If you go out, do something childish and awkward. Be patient and forgiving, and encourage him to be that way. If he feels like he said something stupid or is embarrassed, reassure him that everything is all right. Imagine you did the same thing and how would you want him to react?0THIS IS NOT RELEVANT ANYMORE
Most Helpful Girl
I would stop the anxiety and you ASK him out FIRST!
Then just because you are friends, it doesn't mean you can't be more..
Instead of you 2 trying to find a conversation topic, when you get alone, tell him you know he has had a crush on you for forever, you like him a lot, but are afraid of ruining your friendship... THEN lean in and kiss him...
If the kiss goes alright, take the next step and make out with him for a couple hours.. it doesn't have to be sex, but do what feels right.
Some of my gfs have married the guy that was just the "guy on the edge of our group, so and so's brother" that they never thought was date material, but once they went past that point, LIfe was magical.
Just my 2 cents worth...
Nothing ventured, nothing gained...
Those who dare, win...2THIS IS NOT RELEVANT ANYMORE