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What is the sweetest/cutest thing you ever did in early stages dating to totally win a woman over?

I’m in my mid 30s and I have been dating with a focus on a high-quality serious relationship. I’ve recently been on 3 dates with a woman. I like her but she seems like she’s 60-40 on me (60% likes me, 40% maybe still trying to figure it out) so I have some work to do to win her over.

Has there been anything in particular you have done in early stages dating to win a woman over that worked very well? We know women love the small things – things that are cute or unique or sweet or inside joke related. I don’t want to send this woman flowers yet bc its too soon and she actually told me a story of her girlfriend who was dating a guy and he sent flowers after the 2nd date and it was too soon and it made her friend feel uncomfortable.

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12 Comments

  1. I’m not liking how this is phrased. You don’t win someone over, really. They either want to be with you or they don’t. If they’re 1/2 in then go find a woman who is 100% in.

    That said, it’s only been 3 dates. Were I, you, I would continue going on dates with her. If her interest doesn’t climb, then move on. Don’t try to be someone you’re not.

  2. My wife never traveled a before meeting me. So our first Christmas/New Years I got us a trip to Austria and Prague. We spent the New Years watching the fire works on Charles bridge in Prague. Not small but definitely won her over

  3. In my longest relationship I had so far (three years) I figured out what she always wanted to do but couldn’t – for various reasons. And then I made it possible. Shame the relationship didn’t last. We were really good together.

  4. I have said this before but will repeat it here for you now. What works for me is the “Caveman Approach.” It has only failed me on a few rare occasions. When I meet a woman I club her with humor, and carry her away with intellect.

  5. I don’t like the approach of winning someone over. They’re a person whom I am interested in, not a juror that needs convincing. If they like me they’ll like me. Additionally, if they don’t like me until I do some “thing,” that’s pretty shitty.

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