Conversation advice wanted

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So I went to this new cafe type place for lunch yesterday. I had never been there before and the first thing I noticed upon entering was this very cute girl behind the counter. I was the only customer in the place at the time and since it was my first time there, I asked her about the place, what she'd recommend, etc. She seemed quite friendly and offered me some samples of various stuff they served. It wasn't a place where she's a waitress or anything like that so there's no real chance to tip so the thought that she was being "fake" friendly for a bigger tip didn't pan out. I'm not thinking I need to ask her out right away or anything (knowing my luck, she's probably too young anyway), but next time I go back, assuming it's a similar situation and I'm the only one there or there are only a few other people there, what are some things to talk about? I suck at small talk and wouldn't know how to begin after exchanging basic pleasantries.

What you want to do is ask her questions that show you're interested in learning more about her as a person but not in a creeper/stalkerish way.

So a harmless kind of question that leaves her a lot ways to tell you more about herself is to ask her if what it's like to work at that cafe.

That might get her telling you that she's only doing it part-time while she studies or....some other thing. But do you see what I mean? It's an open ended question, the kind my son with AS would HATE if I asked him, but which neurotypical people are used to in small talk and are ways of generating further conversations.

I'll have to think of a decent way to ask something like that. Asking something that mundane just goes against every fiber of my being. The job doesn't look like it would be very interesting so it's hard for me to imagine a conversation stemming from that. I hate talking about my job so I usually expect most people to as well.

Ask her to lunch with you when it's her lunch break or break time. Get to know her there before asking her out to another place. You say you're 31. Stay away from her if she under say....23. This is only my opinion. I say this because when I waitressed, I got hit on a lot. I felt that anybody who asked me out that was over 25 was a creep-face. I was 19 at the time. The one that made the biggest impression on me was the one that dated me at the place where I worked. He dated me twice - two lunch breaks. But I got this impression that he was married. I found out later that I was right. My manager lived near him and took me for a ride past his house where I saw his wife and kids. I was SOOOO embarrassed. She didn't have a problem with my lunch breaks but she did look out for her girls. In the restaurant business you see a lot of SOCIAL.

Employees are typically required to be friendly whether they get tips for it or not.

That being said, when I worked with the public I was sincere in my friendliness, however I was friendly to everyone, so be advised, just because a woman is friendly does not mean she is interested in dating you.


Whether you are too old....well at 31, if she's under 22, I'd say...maybe. A lot of women in their 20's will date a man as old as 31 but usually this is women in their mid 20's.

I would avoiding opening the conversations with invasive questions. She doesn't know you and probably doesn't want to tell you much about herself at the moment. It'd be better to open with some type of neutral statement that gives her the opportunity to respond, like "It's a really nice day out," or something of that nature. If you do want to open with a question it should also be a neutral one like "Do you guys get really busy in here?"

[quote="KazigluBey"]
What you might do, and I've considered this myself, is a mental check list of maybe four to five things to ask about when meeting a new person.

A couple of examples:

* Going to school? Where?

I highly advise you strike this questions from your list of things to talk about during a first conversation with a potential love interest, especially if she is much younger than you.

Asking such a question so quickly if there is a large age difference could very easily earn you the "creep" label because she doesn't really want to give men she doesn't know information about where she can be found.

I'd also tread cautiously on the asking her about activities she likes to do. It's a very clear "I'm interested in dating you" sign and I don't really have a problem with a guy getting to the point myself, but apparently a lot of NT girls/women don't like being picked up when it's immediately clear the guy is trying to pick them up because they don't want to commit to a date with someone they haven't had the chance to get to know just a little.

So if you do ask this question it might be more strategic to ask it towards the end of a conversation.

Well, the good news is that I made it back and talked to her a bit. She still seemed really friendly and I learned a bit about her (yay). The bad news is that I believe she's already in a relationship. (boo). Oh well, maybe next year.