How/should I ask out a friend/acquaintance?

I am a guy in my 30s. Over the past two years, I happenedy to make really good friends with two women and have become rather close with them. One of them has a friend that I have semi-befriended. Until recently, I had only seen her in larger groups and never had much of a chance to chat with her one on one or in a small group. We’ve actually never hung out just the two of us. I’ve always been really attracted her her physically but my initial impression is she was too much of a spaz. However, after hanging out with her in a small group a few times, I’ve realized she is actually super cool, not surprising since she is friends with one of my good lady friends.

I randomly signed up for OkCupid and saw her profile on there near the top of my list. We had an absurd 98% match based on their algorithm.

I’ve always been hesitant about dating someone in the same friend group and I really value my friendship with our mutual friend. I don’t know what do. I developed a bit of a crush on her it seems, which feels kind of awesome, but I have no idea what her thoughts are towards me.

It’s kind of a delicate situation. I might have already been friend zoned a bit at this point. I thought about trying to get to know her a bit better before asking her out on a date given the context. I’m perfectly fine just being friends with her but I don’t want to make things awkward if she rejects me.

To make matters worse, I told a couple of our mutual friends I thought she was really attractive so it’s possible she may already be aware. It’s not a gossipy group but you know how that stuff goes. What should I do? Any tips on trying to make that conversion?

At this point, it's a good idea to man up and ask her out. If she declines, move on and see other women, put it behind you etc.

I had to laugh about the spaz comment. What made you think she was a spaz/first impression?

Do you think if I ask her out for a date and she rejects me we can still hang out as friends without it being wierd/awkward? I don’t care about getting rejected whatsoever, it’s the friend dynamic that concerns me.

I mean she is kind of a spaz, but she is also really hilarious simultaneously.

If you want a woman, stop worrying about being her friend. It just tells me you're on shaky ground/trying to scoop up sloppy seconds (not confident). You've already got a crush on her. This means being friends is not the best scene for you. In your best interests, I'd suggest you move on from her after that (if she's not interested in you) and start making new female friends and dating other women.

If she's as hilarious as you think she is, she'd have enough wits around her too to joke about things and keep things lighthearted.

I guess asking someone for a date doesn’t have to make things awkward. If I go about it in a pleasant, non-creepy way, there is really nothing to be embarrassed about right? I’m just expressing genuine interest.

Also, this isn’t my only option by any means. Just don’t have much experience dating someone from my social circle.

I don't believe it has to be awkward. Remain a gentleman. You would have done your part.

If the woman you're asking out on a date responds in a less-than-lady-like way or is rude to you, that's on her. Not on you. Remember that you cannot cover for the failures or shortcomings of others.

If it's a group of friends, yes, if the relationship goes bad, it could jeopardize friendships.

No problem - So make her a friend and date other women. Simple. You only need to find one girlfriend.

My buddy has asked out at least 7 of my girl friends. And they all rejected him. And you know what, we all still hung out together! And he's now over the moon happy with his wife. So, ask her out. The worst is she says no, and you move on. Now if she was your best friend, you need to mull it over some more. But she's just an appendage friend.

I married an appendage friend. So, if you like her, you like her.

If she is a match online, maybe wait for her to make a move. I would opt to ask her to something one on one. Or you can play it off as "hi, fancy meeting you here :) online. " and if she isn't interested, she won't be offended because she may interpret you as just pointing out the coincidence and if she is, it may be an opening. I normally don't say this, but i might inquire with your female friend who knows you better "hey, this is kind of random, but i want to ask an opinion. I am on a dating site and i got some matches and one of them ended up being X. Do you think it would be weird if i asked her out?"

Would she also see this match notification? Excellent you signed up for some dating apps. Now start messaging and meeting women who have not "friendzoned you".

OkCupid and saw her profile on there near the top of my list. We had an absurd 98% match.

I’ve been on more online dates than I can count. Most of my friends who are married or are in LTR met through mutual connections, so I thought it might be worth a try. It’s hard to say if she has friend zoned me or not. We haven’t had a lot of one on one talks, so really no way to know.

I guess I’m struggling with how to phrase things as to be respectful/gentlemanly, show that I’m serious, but also give her an easy out if she isn’t interested so we may remain friends. If I could get her alone for a bit, I’d like to say something like: “After seeing more of you around lately, I’ve developed a curiosity about you, do you want to go on a date sometime? If not, no pressure/worries”

I had her alone a few moments the other day but couldn’t pull the trigger, how does the above sound?

I guess I’m struggling with how to phrase things as to be respectful/gentlemanly, show that I’m serious, but also give her an easy out if she isn’t interested so we may remain friends. If I could get her alone for a bit, I’d like to say something like: “After seeing more of you around lately, I’ve developed a curiosity about you, do you want to go on a date sometime? If not, no pressure/worries”

 

I had her alone a few moments the other day but couldn’t pull the trigger, how does the above sound?

No. i would not say ANYTHING like that. I would just say "hey, do you like Mexican food? i have been looking for someone who would want to try out the new place in town with me. Are you game?" Or any type of food or dessert you know she likes -- or any activity she likes. if she doesn't want to go out with you, there is no burn there.

Do you think if I ask her out for a date and she rejects me we can still hang out as friends without it being wierd/awkward? I don’t care about getting rejected whatsoever, it’s the friend dynamic that concerns me.

 

I mean she is kind of a spaz, but she is also really hilarious simultaneously.

Depends on the maturity of the group. Personally I wouldn't care. If they're good friends, it won't matter. If it gets weird/hostile, you're in with the wrong people. Ask her out. Friends are easy to make, finding that special one is a lot harder.