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Last year, I started working for a small-town Denny's not far from where my parents live. I wasn't exactly out yet, but I had requested that my coworkers call me "Eugene" and avoid female-specific petnames like "little girl" or "missy". I'm pretty sure you've seen me mention that place.

While I worked there, a regular customer who was friends with my big sister (Sarah, who also worked there at the time), met me and seemed to become immediately curious. I was off shift, so he sat down with me and began asking me all kinds of questions: "How old are you?" "Are you in college?" "Are you interested in writing?" "Have you considered journalism as a career?" "Why do you cut your hair?" "Why do you call yourself Eugene?" He persisted in making direct eye contact, leaning forward, hammering out questions like a reporter interviews some local celebrity. He said as much, that it was reporters' instinct and he had a feeling I would become a very successful person someday. It all seemed fine at first, but I gradually became a bit unsettled and found an excuse to end the conversation.

My sister was teaching his son basic Aikido techniques, so it seemed normal when the kid wanted to add me on Facebook. He's about my age. After a while, though, his posts became increasingly judgemental and annoying and I eventually unfriended him. He seemed like a p***k, and we never really talked much anyway. I would occasionally run into his dad in public places and he would immediately recognize me and call me over or approach me to say hi, even when I was busy or with friends. He offered me opportunities to work for his newspaper, to participate in short films and so on, but I declined or answered indecisively to each offer.

Flash forward to this January. I'm living in a little flat in Indiana, talking on the phone to my little sister, who just got off work at a small Chinese cafe equally close to where my family lives. She says, "Oh, your friend from Denny's was asking about you." I was confused at first, but then she described him as a middle-aged Hispanic man who owns the local Hispanic newspaper. Red flags immediately went up as she told me that the man had asked where I was, how I was, and then proceeded to go on and on about how beautiful I was and saying things like, "Eugene is such a perfect name for such a lovely girl." He also said that I got along oh-so-well with his son, that we talked for hours and hours, etc., which was an absolute lie.

My little sister accidentally let slip that I was returning to Texas. I told her to tell Sarah about the problem, but Sarah would hear none of it because she thinks the man's an absolute, cordial doll. Instead, the next time the man visited my little sister at work, she told him that I had decided to go back to Indiana.

I'm hesitant to work anywhere near my house for fear he might find me again. He gives me bad vibes and red flags, and I don't want to talk to him, see him or have anything to do with him. The fact that he would start bringing this up with my little sister is even weirder and, for me, that crosses the line of privacy. I've considered what to do if I meet him again, and the only idea I've gotten so far is to tell him the truth about my gender identity in the hopes that he cools off and leaves me alone. However, there are obvious risks to that.

How would you handle this situation?

I'm with Jean on this. Keep as much distance as possible. I'd do everything I can to not out myself. It just doesn't seem like a good idea in the slightest.
Hope things look up. :/

Same as Jean Noh, trust your gut! This man gives really bad vibes and I'm only reading about them online, brr... To me they appear very nosy and obviously they're very good at getting information, that's how it seems to me. Clearly he is targeting you, so if you can, stay away from him or if you happen to meet, you could tell you don't have time for them and leave.

I got the impression that he actually is trying to dig out your gender identity by putting "Eugene" together with "girl", if people would possibly correct him, but he seems awfully interested about your way of identifying anyway, and not in a good way. As said before, it's none of his business, but he's digging up anyway. That's just RUDE. You don't have to explain anything to them, I think it would be wasted on them. Sorry if that sounds cold.