Should I ask her out one last time?

[robertm70]

This is a strange one that I was reluctant to post here but I need some advice. I have a huge crush on a woman and I don't know what to do about it.

I typically don't have issues asking someone out but this case has got me stumped and confused like a boy in middle school. I frequent a very high end lounge that is across the street from the office. I have a friend (male bartender) there that I have known for about 8 years and we have a great rapport. We know each other from another bar and had some very causal mutual fiends but I would not consider him a close friend.

Anyways, I have spent time at this lounge gone through a 2 year relationship, two ailing parents as well as a new business start up. The place has kind of become my social hangout/hideout from a lot of stress in my life but I don't take it seriously (at all).

Anyways, to make a short story long, there is a female bartender whom I have gotten to know who I find very attractive. I have gotten to know her over the past couple of years and find that we have lot in common from love of exercise, to where we chose to holiday, diet and a bunch of other lifestyle similarities (a perfect match). She is also very independent and seems to be careful about the people she dates which I find attractive. In the beginning I liked he but always treated it as a bartender/patron relationship as one should. I am under no delusions about picking up attractive bartenders and never through twice about it until recently.

it seems that we have been connecting with a lot more over the past year I.e. eye contact, frequent return trips to my space at the bar to talk about her personal life and what she has been up to I.e. Dinner parties, vacations etc. I seems to be getting sold that she is a good girl who is not a party animal i.e. it seems as though she was showing a great deal of interest in me. I should also mention that she is 33 years old (not a kids bar/lounge).

About 5 months ago I started to really fall for her and decided to break my code about asking out bartenders. I asked if she was seeing anyone and she said she had an on-again off-again boyfriend. She looked a little taken back so and uncomfortable so I felt I had crossed the line. I cant remember exactly what I said but I figured it was not a big deal and left it at that.

At this point she really turned on the "glances" and "stares" whenever I would come in. I was always careful not to make it awkward but it was clear there was a still a great deal of attraction between us.

At this point my friend (male bartender) started pointing her out to me subtlety. He made a lot of subtle comments about her i.e. that she was single but intonated that I should "go for it" but not very obviously. I was always careful about not coming across as a stalker or weirdo. I didn't want to put her in that awkward position of having to tell me no again but by now I think we would be an awesome match and I am really falling for her. To make matters more confusing, she talked about her weekend away with her boyfriend a couple of weeks back.

 

Anyways.

About two months ago she was back to telling me stuff such as describing places she enjoyed eating in particular brunch places in the neighborhood (in great detail). She was also doing a lot of staring/eye contacts and body language stuff again. It again seems as if she was tying to gain my interest (not that she had stopped). I decided to ask if she would like to grab brunch sometime as friends because I lived in the neighborhood and didn't have lot of friends there. She laughed and dismissed it quickly and moved on to whatever she was doing.

 

There it was, I had my answer. I asked twice and gotten rejected both times. Again, I am perfectly ok with this but it seems that her program has not stopped. Two weeks ago she causally told me she was single and being careful about walking home at night etc. Last weekend she gave me the full story about being single and having going out two a couple of places that I had suggested in the area. My bartender friend had also intonated again that she was single and subtlety encouraged me.

 

I'm very confused about what is going on as it seems like her interest level in me is climbing but now I am in the twice bitten, three time shy mode. I just don't know what I should do about this. I feel like we would be an awesome couple and that we are a match on the compatibility matrix but I cannot get over the fact that she is a bartender and its her job to be nice to me. Its also her job to be professionally single. I don't leave huge tips and I don't play bigshot. I just hang out and for a couple of beers once or twice a week and chat. This might be a "try harder stupid" or "we are just friends". I cant figure this one out for myself.

 

I am reluctant to talk to my bartender friend to much about it as they are co-worker and think adults should be able to figure these things out for themselves...but this one has got me really stumped.

 

 

Anyone have any thoughts on what I should do?

[kassy]

Ask her a last time and then if she says no be done with it, if she says yes you're good to go.

[LilaMarie]

Sometimes the first time I say 'no' to a guy when I'm caught off guard or there are people around...hmm how about you write your number on a napkin? You are letting her know you are interested but put the ball in her court and you are not making her uncomfortable since she's at work. What do ya think?

[angel.eyes]

She has turned you down twice now. Let this go.

 

It's her place of work. She has to be nice to you because her job depends on her being nice to customers. She doesn't have the option of ignoring you or giving you the cold shoulder.

[xcupid]

Three strikes and you're out. Ask one last time. It's a no go then move on.

[robertm70]

Funny because I have thought a lot about that but sometimes I feel like I know her to well now to do that to her. I prefer to be forward but this is a strange one for me. It feels like its supposed to happen but the fact its a patron/bar tender thing puts some weird dynamics in the mix.

Five minutes with her somewhere else and I think it would be a done deal. Now I think I'm getting in my own way on the issue I.e. rules, ideas etc.

Maybe I need to take once last attempt at it. I'll give her my number and forget about it if it doesn't happen.

Thanks for the advice.

I'll post back and let you know how I make out.

[robertm70]

She has turned you down twice now. Let this go.

 

It's her place of work. She has to be nice to you because her job depends on her being nice to customers. She doesn't have the option of ignoring you or giving you the cold shoulder.

 

 

I would agree with you 99% of the time. That's why I'm here. I'm certain I'm not delusional about this. I think I just need to clear the air so I can move on. I have been guilty in the past of missing all the signal. Now I just need an answer one way or the other.

[truth_seeker]

Where did you ask her out twice? I read about brunch but what was the other time? Are you sure your bartender buddy isn't messing with you with false encouragement? She sounds like she's into you but is also playing games.

 

You want to know if she really likes you? TEST HER. Go in one night and order a drink from her. Be polite, say hi, then walk away. Go to another area of the bar and chat up other women. Wait a while, then go back to her for another round. Don't engage in any conversation with her. Grab your drink and go back to the other women. Keep chatting up the other women, say goodnight to your male bartender buddy, and leave.

 

The next time you go to the bar you will know right away if she's into you. If she's into then the test you did will have gotten her angry. If it didn't bother her, then she's not into you.

 

If she is angry then use this against her. Tell her you asked her to brunch but she blew you off and talked about a boyfriend. You took it she wasn't interested in you and didn't want to bother her while she was working. Offer to shake hands and say "forgive me?" with a smile. If she bites on this, then say to her "let me make it up to you, brunch on me." Give her your card and tell her not to be like everyone else. Text or call you so you two can meet up.

 

If she turns out to be a b-tch, ignore her, pick up some women right in front of her face. Show her you're the man and don't need her.

[introverted1]

You've asked twice and she knows where to find you. If she wanted to go out with you, she'd find a way to ask you.

[LilaMarie]

I'll just add my ? .02

 

 

Isn't flattering that a guy can't get you off his mind and is persistent? Let us not forget that chick flick The Notebook. Yes, I'm a romantic. Go for it once more, I'm cheering you on!

[oberkeat]

If a woman turns me down once, I never ask her again. I make a once-in-a-lifetime offer.

[thecrucible]

I'm not sure but you said you asked her out initially "as friends" so it could have sent out the wrong signals. You could have been bold and suggested going out together somewhere.

[robertm70]

Where did you ask her out twice? I read about brunch but what was the other time? Are you sure your bartender buddy isn't messing with you with false encouragement? She sounds like she's into you but is also playing games.

 

You want to know if she really likes you? TEST HER. Go in one night and order a drink from her. Be polite, say hi, then walk away. Go to another area of the bar and chat up other women. Wait a while, then go back to her for another round. Don't engage in any conversation with her. Grab your drink and go back to the other women. Keep chatting up the other women, say goodnight to your male bartender buddy, and leave.

 

The next time you go to the bar you will know right away if she's into you. If she's into then the test you did will have gotten her angry. If it didn't bother her, then she's not into you.

 

If she is angry then use this against her. Tell her you asked her to brunch but she blew you off and talked about a boyfriend. You took it she wasn't interested in you and didn't want to bother her while she was working. Offer to shake hands and say "forgive me?" with a smile. If she bites on this, then say to her "let me make it up to you, brunch on me." Give her your card and tell her not to be like everyone else. Text or call you so you two can meet up.

 

If she turns out to be a b-tch, ignore her, pick up some women right in front of her face. Show her you're the man and don't need her.

 

To be honest, The first time wasn't really a proper "ask out" as much as it was me letting her know I was interested in her.

The second time was an actual ask so I guess you can say I actually have only asked her out once. It was not my best moment for timing when I did it so perhaps there is a communication gap. Maybe I think I thought I was clear but came across as too casual. I'm not really sure.

 

I have chatted up several women in front of her and gotten phone numbers etc. Meeting women has never been an issue for me but like most people, finding someone whom I'm compatible with is difficult.

I've even had her "seem" angry with me a couple of time. Once she even refused to shake my hand and made up some excuse about something on her fingers but I could see that she was pissed off in her eyes. A couple of friends I was with even commented on it. Again, I have been very guilty of not seeing or responding to signals in the past. That said, I am not a player and she knows it. She even asked me what my "type" was one night I told her it wasn't the type of women in this bar. I prefer more down to earth type.. which she is.

 

It's time to ask the question again and see what happens.

I'll keep you posted.

Thanks for the advice.