I'm better at that myself as well.
Soo, after my three OKC strikes I'm a bit hesitant but I did agree to meet a guy for ice cream. We've talked a bunch and he seems cool, but definitely not getting my hopes up.
On another front, here's a little story: Two years ago, when I was on my big birthday road trip, I met this super cute guy (DT fan, btw) who worked at a brewery in Idaho. We exchanged numbers and I was totally crushing on him but I assumed nothing would come of it because he lived in fucking Idaho. Well, he ended up moving here. He contacted me... maybe sometime last year?... to tell me that, and we eventually met up for a beer. I was finding him hard to read and nothing happened. We went our separate ways and neither of us reached out to the other for a long time.
Well, Wednesday I was in search of a pack of gum while on the road for work and I happened to be passing the store he once told me he worked at. My gut told me to go there, so I did. Turns out he no longer works there (and they had no gum), but I still had his number so I texted him to say hi and we kept talking. We made plans to get a beer next week and just kept texting a bunch over the next couple days. I was getting a bit of a flirty vibe so I turned it up a notch to see how he would respond. He asked if he could sweet talk me into meeting on his side of town (we live maybe half an hour from each other) and I asked "What's in it for me?
" which led into some innuendo. I later told him I was going to an amateur porn festival so the conversation went in that direction. I made a sort of joke about showing him this hilarious-looking porn I recently bought, and he said something like "That would set a different tone for the evening. Totally down." Today he texted asking how my day was going while I happened to be taking a selfie of a Halloween costume I've been working on, and I ended up sending him a pic that involved some cleavage... which he commented positively on.
Anyway, the reason I'm going into detail about all of this is because I'm always so uncertain about whether I'm reading signals correctly, but at this point I think it's pretty obvious he's in the same boat as I am. Now the question is whether I will have the ovaries to actually say something and/or make a move if he doesn't. I'm getting better at that but still super shy about it because I'm afraid of being turned down for whatever reason. I know I'm preaching to the choir- I think lots of people (if not most) get terrified putting themselves out there like that. I suppose I don't have much to lose at this point, since it's not like we're close/haven't even talked in a long time prior to this week, so worst case scenario we go back to not talking. Still, I feel like a chicken! We shall see. I am anxiously awaiting Marty McFly Day. Stay tuned...