Dear Dr. NerdLove:
I wanted to reach out to you because I’m seeking guidance on a potential relationship, but am uncertain of how to proceed.
About 2-3 years ago, I went with a friend to a nearby bar, which featured a “Taco Tuesday” special after we had both seen “Sorry to Bother You,” and wanted to discuss it further. Needless to say, the bartender working that night was sociable (especially once I showed an interest in her work and craft) and overall it was a good time.
A year or so later, I came back to the bar one night to meet some other friends. Once again, she was working there and seemed happy to see me. We caught up a bit, and much to my surprise, comped me for one of my drinks, which was sweet and generous of her. This back-and-forth carried on throughout the rest of last year. I’d show up, eat, drink, tip generously, and talk. It turned out we had a good amount in common: she’s a photographer, I crew on film/video jobs. We both love talking mixology and different liquors and liqueurs.
In short, I developed a bit of a crush on this bartender. And after introducing her to some of my friends, they also picked up on a potential mutual interest vibe. So near the end of last year, I expressed an interest in hanging out with her outside of her workplace. She, much to my surprise, gave me her cell phone number and seemed willing to meet. She did express a desire to keep it casual, however, although that was not a deal-breaker for me. As someone who has to be friendly and sociable to keep working, making friends is always easier and slightly more comfortable to me.
So I reached out to her at the beginning of this year to see if she wanted to get coffee. She did text back that she was in favor of it, but we never got a date or time pinned down, so I let it go, not wanting to pressure her. Fast-forward to now, where I stopped into her bar for a meal and some drinks. She was working there and seemed very happy to see me, so much so that she came around the bar to sit next to me as we both talked about our lives. At this point, even I felt like there was some kind of chemistry between us, and this was before the liquor started flowing.
Later on, I sent her an invite by way of a text message to a casual event among friends, but she didn’t respond, though I didn’t take it personally. Given her desire to keep things simple, I figured pushing her for an answer wouldn’t be helpful.
So in summary, I’ve been interested in getting to know this bartender a bit more outside of the place she works. We have common interests and goals, and seem to get along well enough when at her workplace. The question is where the boundaries for this relationship are.
If it can be romantic, that would be fantastic. If it’s more of a friendship, I would also enjoy it greatly, since I find myself cherishing those the most. If it’s more of a casual acquaintance-type of deal, I also would be willing to accept it, since the matter would be settled. The issue comes down to asking whether there’s room for this relationship to grow at all outside of the bar.
I’ve read enough articles and essays to know how often women have to be diplomatic when refusing the advances of men, and the difficulties of navigating that space safely. Therefore, I’ve tried to avoid overstepping my bounds with her or violating what trust I’ve earned.
Any advice or help you could provide here would be greatly appreciated.
Thank you,
-Searching for Boundaries
