Well firstly when it comes to talking to women I'm clueless. I don't know what may be considered flirting, because I try to find out more about the girl. Yet to me trying to find more about a girl is just being friendly. When it comes to trying to make her laugh I tend to try and get everybody to laugh, which leads to my second question. How do I let a girl know I'm interested in her?
Most Helpful Girl
Just go for it. And I don't mean tell her your interested. When your talking to her be very consistent, talk to her in person or message her 3-4 times a week. Ask her questions about herself; what she does as hobbies, activities or work and make sure you sound interested! Ask a lot of questions about her interests as well because then she will feel like you do care. Also compliment her; compliment how her hair looks like "Oh did you cut your hair?" "No?" "Oh its looks great today" Shower her with compliments!!! That is one way of flirting just in case you still don't know her very well. You can compliment her twice in a conversation but anymore than that is creepy.
Also arrange a date with her after you guys feel comfortable, say "Oh have you heard of this new movie called ____?" "Yes/No" and she might share her thoughts on it and you say "We should go see it this weekend, it sounds really good!". And she will say yes or no - that will give you your answer as to whether or not she's interested in you back! Also don't be afraid to say something goofy, its nice when a guy isn't serious all the time and can let loose sometimes. Just shows you can have fun :)0
Most Helpful Guy
I used to be in the same boat as you, though there is still quite a bit I'm getting sorted out.
Honestly, the best thing you can do is ask her out. See, flirting, to me, is a largely fruitless and frustrating practice. I say this because it's much too easy to see being nice as "flirting". That or you might think you're being totally obvious, but the other person is, well, as you've said, "clueless".
Again, I really think that if you want to help yourself out in this regard, your best bet would that if you like a woman, just ask her out. Trust me, I know it's very intimidating, especially if you have little to no experience with it. Even more so if you're into your 30s and don't know what you're doing (seems to be a very common thing these days for some reason).
You ask her "would you like to have coffee with me", "would you like to have dinner with me", or something along those lines. Whatever it is, make it clear that you want her to do it WITH YOU. "I'm going to x-fun public event on Sunday afternoon. Would you like to come with me?" Don't ask her to "hang out". Friends "hang out". Make it clear that you want to do something that sounds fun and that you want her to be there with you.0