Recently, I moved from a small town to a big city in the Pacific Northwest. There's a bar by my house and I met the female bartender about a month ago, coming with a friend. Turns out that many LGBT crowd tend to frequent the bar, some of whom became my friends, and I happen to be one of a few straight males to go there. There are many couples but not many single straight males. (Just got divorced btw.) I liked this woman from first sight. Two weeks ago I said something disrespectful and when I came to apologize two days later, she was very friendly, telling me about herself, asking me about my family, flirting, jokingly touching, hitting me with the paper towel roll, and even giving me her phone number. When I told her that I have a family in Israel, she was joking about me taking her there.

I feel that I have an excellent rapport with my neighborhood bartender. But it's hard for me to tell whether all these signs point to her desire to take the relationship to a higher level, or merely her attempt to be friendly and regard me as a good friend instead of just a customer. I'm conflicted about whether to ask her out, preferably with our mutual male gay friends so that she wouldn't feel pressured on a "date" or should just wait and let her take the lead (or time do its course)?

I have to note that she does rub my back, smiles a lot, and flatters me about my smartness, knowledge of music, my Karaoke singing, and other things. What do I do, Dan?

Amorous In Portland

Ask her out.

Gotta keep this one short, as I'm getting on an airplane. But quickly, AIP: While it's usually a Very Bad Idea to assume a friendly waiter/barista/bartender is interested in you romantically—the same goes for very flirty waiters/baristas/bartenders—the exchange of phone numbers and the back rubs and the paper towel rolls would all seem to indicate her interest extends past your big tips. But there's only one way to find out: Ask her out already, AIP, and don't fudge it by asking her to hang out with you and your gay male friends. Tell her you'd like to take her on a proper date—then quickly add that if you've misread a signal or two or three, you're sorry, you hope you didn't make her uncomfortable, and you can take "no" for an answer like the grownup you hopefully are.