I would appreciate any advice people can give me on this! I am 31 and only just starting to get confident dating. I've mostly met people through online dating, but I know this woman from work. We both swiped right on Tinder, so technically it wasn't a date through in person interaction, but I'll take it...
Anyway, first date was fantastic! We met at a bar and talked for about three hours, she decided to ditch dinner with her housemate to continue the date, and when we both realised that there were no food places left open as it was late on a Sunday night, we went and got some ice cream instead. She had touched me a couple of times and vice versa, but there wasn't much of it. I am still a bit timid with this, especially if there's some distance between the two of us, but I did close the gap to do it a few times. She never seemed irked by it, and seemed enthusiastic about a second date when I mentioned it after walking to her car.
We talked over text later and I asked her out to an Italian restaurant she had raved about. Unfortunately, the tables were large and we were seated across from one another, so there was no opportunities to touch during dinner, but we greeted each other with a hug and kiss on the cheek, and I took a few opportunities to touch when I could. After dinner she suggested going to grab a drink, so we moved over to a bar. Again we talked for hours, definitely felt sparks (from my end at least, but I think for her too), and I got some more courage to reach out more often. I tried to create opportunities to hold her hand (i.e. putting my hand on the table quite close to her) but she didn't meet me half way, and it felt awkward trying to push it, however throughout the date she never pulled back or gave any signs that she was uncomfortable with my touch. As we were walking back to her car I did put my arm around her waist, and she reciprocated for about a minute, but then pulled away. At the end of the date she gave me a tight hug and again seemed enthusiastic about a third date.
She texted me the next morning to thank me for a wonderful time. Since then I've texted her just to chat, and we had a couple of texts back and forth, but her last text was just before I was going to bed and didn't feel it was the opportune time to ask for another date, so just said good night. I'm planning to text her again in a couple of days to ask.
So the reason I'm asking for advice is that this is doubly difficult for me, because I'm linked to her professionally. All the difficulty I have with worrying about coming off creepy or like a sexual predator by touching/flirting is much higher in this circumstance. I am unsure if the lack of a kiss, let alone the physical intimacy, is a clear sign she's not interested, or if it just means she might take things slow; or if it means that I have to just step up and go for it, push the boundaries (but obviously stop immediately if she pulls away or shows any other signs of not consenting/being into it). I know that conventional advice is not to get hung up on one woman, to keep looking around and dating others (and I am doing that), but she is an amazing match, so if there's something I can do to move things forward then I would love to know people's advice.