After going through an emotional roller coaster a couple of years ago with an ex, I think I'm finally ready to try dating again. Only issue is, I graduated from college already and don't have any means to naturally come in contact with women (like work, classes, etc.) so I could approach them. Obviously I see strangers all the time but I'm too averse to it. There is is cute chick at the gym I go to and I've been meaning to strike up a conversation with but since I've been out of it for so long, I just feel awkward trying to put up a persona and ooze confidence without really wanting to, I just wanna have a normal conversation. However, I'm weird, like really weird. The type of jokes I make are situational and they can be funny, but conversation wise, I just don't know how to do it. Here's what I was going to say, and it honestly sounds like a horrible comedy movie:
She was cleaning a few of the equipments laid out and she (by the way kinda looks like Katy Perry, real talk) was cleaning something I was about to use. She told me to wait a second and I said alright, this was the opportunity to naturally talk to her since words started coming out of our mouths. Next thing you know the first thing I remember I used to do was compliment people and make a slight joke about requiring there services and that I pay handsomely. It ran like this in my head, "Hey, your pretty good at cleaning, mind coming over my place and clean it up for me?" Then I just wanted to smack myself in the face for even thinking up something like that, I just stayed shut and didn't want to look like an misogynistic idiot. I'm certainly not a misogynist but I can be an idiot an times. The whole reason I'm interested in her is cause obviously she's cute and we've shared a gesture and eye contact every now and then, maybe I'm just gassing myself up but I need something to hold onto!
Only strong quality I know I have is that I'm a really good listener. I'm a funny guy but I don't know how to get that edge, be a charmer, or make a conversation awkward... Any help?
There's so many things you can play around with the scenario you said. I would've made the joke with the current uproar with Ebola; I would've said something along the lines of, "Doing your part in Ebola prevention.. I approve." And see how they respond from there.