What might be read by a customer as "personal information" is probably the barista doing her job by making small talk with her regular customers (especially if those customers are good tippers). Sure, she might tell an anecdote, talk about a band she likes, or share a tidbit about a fun weekend. That is what people in the service industry do! I tend to frequent the same cafes, restaurants, gym, etc. and have dozens of these small exchanges with staff members every week. The waitress will usually remember my order, ask about the project I'm working on (I'm usually typing on my computer), and tell me an "update" about something she mentioned the last time I was there. I tend to be friendly/chatty when I regularly interact with the same prerson. But I really would not expect them to tell me about their dating life-- that seems TOO personal for these kind of casual interactions. i would guess that, because of the large age difference, the barista never suspected that the OP had romantic interest in her. Therefore, it would never occur to her to diffuse his feelings by dropping a hint about the boyfriend. I mean, why would a young woman randomly tell a male customer her father's age about her dating life? That's not typical. Its also possible that she made up the boyfriend as an easy-out for turning down her customer. It's just an uncomfortable situation, regardless of the age thing. I stand by what I said; women whose jobs revolve around being polite and chatty with customers for tips usually don't want to be asked out on the job. Sure, it happens all the time. Lonely men misread their friendliness as sexual interest. But it still makes it uncomfortable. It's awkward when doing your job well and providing friendly service is misread as a desire for friendship/romance. That's why I think it's better to look for dating partners in places where you know there are available, single people looking to date (online dating, matchmaking service, meetup.com, social clubs, activity groups, etc). That's where you are going to be successful. That is where people are going to be friendly with you because they like you and want a friendship/romance-- not because being friendly is their job.