I'm not exactly a stranger to dating. However, here I am looking to pick the brains of all you helpful and insightful readers.
Last Thursday I had a second date with a woman I find myself liking more and more. The first date was one week prior. The backstory, as quickly as possible: This woman, "Mary," I'll call her, and I have been casual friends for 15 months, hanging out in groups on occasion, whether at a bar or watching a movie at her house. I was briefly involved with a somewhat close friend of this girl's back in March, but this seems to not be an issue, as far as I can tell (her best friend suggested several times in the past couple of months that I ask "Mary" out, in fact). I date a good bit but never ever serially. This girl is the first in a while that I can actually click well enough with to at least see the possibility of something real, and I'm totally cool with giving it time to develop in that way. I could have patience with her and with myself.
The first date went extremely well with over 5 hours of conversation and lots of laughter. I'm not big on the cliche end-of-first-date kiss, and neither of us gave the other the impression that it was wanted at that moment when I walked her to the door. I'd say we're both pretty shy and reserved, but not painfully so. We each told the other over the next couple of days that we had a great time and should do it again. So I asked her out again and we've been texting here and there. A goodnight text from her several nights ago (after I watched a movie with her and a couple of mutual friends at her house) and an "I'm looking forward to tonight" text a few hours before the date. We had a great dinner then played bocce ball and sipped on good beers for a few hours. (We were supposed to go to a comedy improv show, but we lost track of time and completely missed it!) After bocce and beer, I suggested we buy a bottle of wine and enjoy the warm night at the playground park near her house before we called it a night. She said one of her friends was down and had made her feel guilty about being busy instead of hanging out with her. I took her lead and acquiesced, saying we'd go back to her house where she'd left her phone. We eventually met up with the friend at a bar very near my own house, and "Mary" insisted she drive separately so I wouldn't have to drive the 10 miles back to her house when I'd already been driving all evening. So we became a trio hanging out in a bar, and it continued to go well despite that. She even mentioned hanging out again soon. But my desire to take the date into a more intimate realm was obviously nixed. Outside in the parking lot at closing time, she gave me a long and very nice hug and said thank you and she had a really great time. Her friend was standing 10 feet away, so clearly it was not a first-kiss moment.
So the next night she and I ended up hanging out in a group of mutual friends after she invited me to join them. We ended up being the last two at the bar after everyone went home. We sat and talked for a couple of hours then I walked her out to her car. We shared a long minute-long hug then she asked for "more hug!" Then I kissed her for the first time, briefly but nicely. She seemed excited visibly and texted me on her way home thanking me for "a great night!"
This past Sunday evening she and I and, again, mutual friends went to a haunted house attraction. While we were all walking through the pitch dark in a single-file line after being instructed to keep a hand on the person in front of us (I took the place behind her, of course), she pulled my arm around her and held my hand for a moment. A bit later she did it again and we walked very close together.
I texted her "how are you?" yesterday and she finally responded after a couple of hours "At work, boring day, phone was dead all day." She goes to school during the day and works at night and so this past evening I decided to ask her out via text since a call wasn't going to get the job done.
It's been 10 hours since the text asking her out for the third date and there has been no reply. She's a pretty avid texter, I should point out.
Sorry to be so long-winded, and I appreciate you reading through all of this. What are your thoughts? I know calling on the phone tomorrow is the best option, but in the meantime, I am so confused. Do you think things are still going well? Thanks so much.