How do second and third date requests actually work?

Forget about the first, I wanna ask about the following dates.
I was always under the impression that you usually only ask the person on another date after the actual date is over, but things didn't progress that way this time.

We were still in the middle of dinner when he asks me if there's any place I'd like to go on our next date. It wasn't this smooth because I was a bit lost for a while, but then he says we will go wherever I want (granted it's within the country!) and if I can only make it on a weekday that's also fine because he can take a day off work...
Now wait, he was being serious there. I didn't want him to take days off to go on a date with me so we made it a Saturday, but is this normal or what?
I can be a bit dense I guess, that's why only now I'm thinking about such things, but isn't this a bit extravagant?
I'm not a country girl, but I like simple things.

How do you guys actually progress from one date to the other? Anything you do different in terms of location, conversations, etc?


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What Guys Said 1

  • It sounds to me like he was overly-eager, which is often a sign of insecurity and self-doubt. A lot of girls find it a turn off for that very reason. And usually guys who have a bit more dating experience, know not to come off so desperate. Especially on the first date.

    Your initial instincts are correct. It is far more natural to suggest a second date when the first is over, or even to wait a day or two so that you both have time to process how you feel, without pressure.

    To basically say we'll go anywhere YOU want, and at ANY day you're free, even if it means I miss a day off work... that really smacks of desperation. And he's giving you very little to work with if you don't want a second date. I mean, you're pretty much reduced to saying "It's you."

    • Thank you very much for your input, that's very helpful.
      Indeed I would have maybe run in the other direction if I haven't known him for a long time. Not because he came off as desperate, but because I start wondering why is he in such a hurry for. (I've had my share of guys who want to sleep with you right away, but then again they don't ask you on a second date so promptly either). So it was just weird.

      Like I said, we've known each other for a while, but not really talked one on one. His friends were always hinting at me that he's a great guy, just very shy, but I wasn't sure what to do at the time.
      But apparently he's had a crush on me for the last 6 months I guess and that's what makes him all nervous. He tries to act cool and gentleman at the same time, so I tend to forget that and act all shy myself... What to do, right? Sounds like we're in trouble, haha.

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