I am recently single after a serious two year relationship. I've never been too great at even talking to women, hence joining this awesome sub. Yesterday I finally got myself to get out of my comfort zone and just go for it.

I work as a pool cleaner. Yesterday I show up to one of my pools and there are 3 kids running an icee stand across the street. Two young women are there, one of them quite cute (let's call her Amy). So I clean the pool, come back out to the car and the kids call me over to buy an icee. Cute girl or not, I'm a sucker for things like that. I buy an icee, laugh with Amy about being their only customer and leave. At the next pool I remind myself that meeting girls is just going to take practice and the nuts to ask for their number. I drive back, pretend to go fix something at the pool and get called over again by the kids. I talk with Amy a bit more, she's babysitting the kids, normally baby sits the kids up the block a ways, a few comments about the icee stand etc. As I'm about to leave, I asked her if she'd like to get coffee sometime. She hesitates, but asks for my number and I go on my way. This is where I thought I screwed up, she'll just never text me. Well she texted me, I asked her about coffee after a bit of pleasantries but she declines. Apparently she works two jobs and doesn't have much free time, which is why she hesitated to get my number. I made a joke about my being a random stranger and that* being why she hesitated. "yeah that too lol" was the reply I got. I apologized for being forward (probably a bad move) and haven't gotten a reply since.

Success': Asked her to coffee. She texted me. Failures: Did not get her number first. Backed down once we started texting.