Does it matter when/how I ask him out?

[joanne1226]

We're both in college and we are on the executive board of a club on campus. We've grown close over the last few months especially; we always find time to talk just the two of us and share personal stuff about our lives/futures. He is very polite and a gentleman and holds open every door for me - we also hug goodbye pretty much all of the time. I know that he is single and my feelings for him are strong. I'm not sure whether to ask him out now/before he goes home for winter break or if I should wait till sometime in January or February. I don't want to rush him but I want to know his thoughts and honestly kind of feel impatient that the subject of us dating has never really come up. When should I ask him and how should I go about doing so?

[RavVid]

OK he holds the doors open for you. That makes me think he will want to do the asking rather than be asked.

You are on a club executive together - so that is business and whilst you might talk non-business it is still in work mode. He may feel he shouldn't mix work and romance.

I just think you are better off to be a little subtle rather say "wanna date me?". I know lots of people will say to ask him.

Look sometimes I have gone out for a meal with a (female) friend and came back from a date. You could easily suggest having a meal together BEFORE winter break then say no business talk at the meal so it is completely social. You could say that you will miss him over winter break. I've had girls say that they are "starting to fall for me".

I think you will get better results that way.

[Guy13]

Polite and Scared often go hand-hand. Somebody has to do it. If you start at a bar beer 🍻 🍸🫒or like see what he does afterwards. If he suggests a different bar next date then his heart is not for you.

[In_Trance]

yes, but not as much as you think it does

[SnowedIn]

Ask him now.

[SnowedIn]

Sorry... hit send instead of return.

Talk to him when you guys are comfortable. Like coffee on a relaxing afternoon. Or dinner after one of your club meetings. Not sometime when he's off to class or worry about something else.

And, as for how, be direct. Tell him you enjoy your relationship and would like to expand it.