I fell for a bartender

Wednesday | June 26, 2024

Love Letters Dating

I fell for a bartender

I am 51 years old. A few months ago, I was able to attend a training in Alabama. During my time there, I met a beautiful bartender. We spent the week chatting with each other. Every night I asked her to go out with me and she would say that she couldn’t because she had plans.

At the end of the week I had to say goodbye because I had to go back home, many hours away. But then I went to another training a few weeks ago, and I was able to see her again.

We continued talking, but this time I was not able to stay after because of a new boss who would check the cameras to make sure everyone was out of the bar (at least that’s what she said).

I want to take a risk and ask her to go on a big, romantic trip, but I don’t know for sure if she will like that or think I am creepy.

Let me know what you think.

– Plans

You asked her out multiple times and she declined your offer every time.

Do not ask her to go on a trip with you. That’s one more question she’ll have to navigate – while at work!

It’s possible she’s been nice to you because you met her at the bar where she’s paid to be hospitable. It’s also possible she thinks you’re an OK guy – but that’s where it ends.

She’s been clear that she doesn’t want more from you. She also told you there are cameras monitoring your behavior.

This woman made you feel happy, interested, hopeful – and maybe less lonely. There are single people at home who can do that, too. Try to meet them on apps or by joining clubs.

Don’t pursue someone who’s at work, especially if they’re in the process of serving a customer (you).

You want to meet someone who could walk away at any moment but chooses not to.

Save the big, romantic trip for someone who has a record of saying yes.

– Meredith

Readers? Can you talk about boundaries here – and other ways for this letter writer to find better company? Tips on reading the room (or the bar)?

Send me a letter – because sharing your questions helps other people feel less alone with theirs. Use the anonymous form or email [email protected].

Bartenders Crush Dating

Featured Comment

“That’s too bad you’ve fallen for a woman who (1) is paid to be friendly to all the customers and (2) you don’t know at all. She makes excuses to keep you at professional distance (e.g., ‘I have plans’ and ‘the new boss checks our cameras.’ She gets hit on multiple times every day. Let it go, and move on. Don’t go back there again. Why are you hanging out in a bar every evening? You can’t think of anything else to do?

Join some activities in the town where you live, where you can interact normally with women. There are a million choices such as classes, clubs, sports, gym, Meetups, volunteer work, church/temple, etc. (And if bars are your second home, consider whether you have a drinking problem–that’s not going to be attractive to any woman who has it together.) Don’t ask a woman to go on a trip for a first date. Try coffee, a museum, a concert in the park, etc.”

JiveDiva Share Thoughts