Should I have told him I’ve never dated?

This is a huge red flag. "We'll just have to make this one and done" can only be one of two things:

1) he'll take you one date to push your boundaries

2) he'll try to future fake you before the date to sleep with you

Just blow him off and move along. If you've ever gone to anything one on one with a friend, then you've been on a date. Friend dates are great, don't discount them as valuable interpersonal relationship experience.

You’re not overthinking. First of all, I don’t see why he asked twice unless he’s mixing you up with someone else (talking to multiple people). Also, “one and done” makes it sound like he only wants to see you once. I’m guessing he has a virgin fetish. A lot of them do.

I didn’t date until 21, and a lot of guys were definitely out to use the inexperience to their advantage. I didn’t put out, which surprised them because they assumed I’d be as horny and desperate as a 21 year old man with no experience. They wish.

I’d cancel it honestly.

In my experience it's not a good idea to tell a man that you're naive at something. (Naivety isn't necessarily a bad thing, as we're all naive at something at some point.) So now, if he's like the vast, vast majority of men, he's got that little bit of information in his brain, that he can do all sorts of shit that you may not flag as a bad thing because you are inexperienced. I wouldn't have told him yes even if it wasn't true. Don't trust that a guy won't lie to you. If the relationship works out later you can always come clean about it... but early on, you don't know this guy at all, and you don't know how he'll take the information. Never reveal your cards early.

You're a good person and you're honest. But bad men take advantage of a woman's honesty. I don't like his comment about "once and done." That makes me pretty upset with him.

In my opinion, his question about whether you've dated before was out of line....please forgive my bluntness but in my opinion he was asking you, in a roundabout way, if you were a virgin. I would not trust him. Very careful. And don't feel like you MUST or SHOULD DO anything. If you want to, you don't even have to go on this date with him. You can cancel. Don't worry about being a "nice girl". I tell you this as a friend and bc I'm in my 30s. In my 20s I did a lot if things bc I felt I "should" and to be "nice." ALWAYS trust your gut. Good luck.

His comment is really off, even as a "joke".

It's weird that he asked if it was your first date too.

Be careful....and here's to many more dates in your future 💗

When ever you think you are overreacting, that's your intuition. The part who thinks you are overreacting is the harmful socialization all women sadly go through. So remember this. Trust your intuition. You are never overreacting, you are naturally reacting to something negative.

In the future, I would not tell men this. Just say you had a few relationships/dates, they just didn't work out. Lie to whatever extent you're comfortable with, but keeping it vague is best and if they press, that's a red flag in itself. "I'm not comfortable talking about this with you" "I'd rather focus on the present" etc.

(edit - typo)

1) Never show men your cards. Don't tell them you're unexperienced, they'll use it against you.

2)

Ew. What?

3) He asked you the same question again, which means he didn't even bother to remember any details you told him about yourself. Extremely low effort. Probably talks to multiple women at once.

4) He really doesn't:

He sounds totally sus. Like he's already carved a plan in his pornsick mind, he feels like he's figured you out. it's better to avoid telling guys about our experience or lack thereof. If we aren't careful, they can string us along till it blows up in our faces. Honestly, I was even more vulnerable when I first experienced limerence till the guy uncovered himself than I am now, so its best to follow FDS to follow FDS to begin with. I am about your age and following FDS changed my life. Follow the handbook and have a more stress-free dating life. Keep safe

Wtf? RUN.

Thanks everyone for the advice. I did call the date off, I blamed it on me being overwhelmed (which is true) and he said he completely understood and left it at that. For a little extra context he did mention that he wanted a long-term relationship and that he didn’t want to hook up. I believe that he asked me if I’ve ever dated because I was extremely awkward and shy during the phone call, but I do agree that it was too personal of a question for our first time talking. I‘ve come to the conclusion that I need to work on myself and my confidence more before pursuing a relationship.

This is actually a good vetting tactic. The creepier they are, the faster u can block them