Tips On Wooing A Bartender, Please

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There is a beautiful (and very popular) bartender. She is 44, I am 34. We have fooled around minimally, but I’ve never asked her out.

Recently, she opened up to me about her life. I asked her what she likes in a man. She said to get on her good side – she likes gifts … and money. Here is the thing: I have known her for more than 10 years. I really want to take her out. It isn’t just about the sex. I know it wouldn’t ever turn into anything considering her profession. I wouldn’t be able to fully handle it.

I have been through a lot, and while I am attractive, I know I still have things to work on. This would be more of a friendship with benefits. She talked to two other people about me, asking what kind of guy I am. They put in a good word. She also got super jealous when I expressed interest in another blonde bartender who also liked me but happens to be married (I didn’t know).

My question is, how should I woo her? She has so many clients it’s ridiculous, guys constantly bring her food, flowers, and such. I am thinking I am going to have to go for something like getting her jewelry, but I don’t want to come off like a weirdo. What do you think?

– Patron


If everyone else is showering her with gifts, you should try something different. Tell her to describe her perfect night off and then offer to deliver it. Maybe you’ll wind up taking her to a restaurant she’s always wanted to try. Perhaps you’ll play bartender, serving her something she loves before the two of you relax in front of a movie.

Her answer might be no, and if that’s the case, please move on. I know you want to hook up with her, but you also need to be with someone who appreciates your time.

Do this soon because a nice night with her might clear up your goals. Maybe at 7 p.m., outside of the bar, you’ll see there’s real potential here. Or … none at all.

You didn’t ask me if you should be pursuing her, in general, as you work on yourself and seek confidence in the dating world. I do have some opinions, but I’ll keep them to myself. Just know that when you’re tired of this, there’s a big world outside the bar.

Please find new scenery a few times a week. That will help everything.

– Meredith

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