So after a year and a bit of dabbling in using a dating app to meet someone and having limited success (I had one first date in 2025) I'm in a slightly unprecedented situation. In January I went on two first dates, and both were with women I'd wanted to see again.
The first we met up at a comedy show and had some drinks and dinner afterwards. It was an ok night, and I felt it was worth another to get to now her a bit better. We had been planning a second date when she experienced some health concerns which have sort of put a pause on things (a hospital visit seems a bit much for only having had one date). We'd been texting and I'd sort of thought that she was pulling back to focus on her health, but I got a text message this weekend that suggests otherwise.
Which makes me a bit awkward because after postponing the second date with woman one I had a first date with woman two. The original plan was to meet up Saturday morning for coffee at South Bank, but the coffee shop we picked turned out to be closed on Saturdays, so we strolled around South Bank and ended up getting juices from Boost juice. We chatted for an hour or so before heading our own ways.
We haven't worked out what we'll being doing but we've tentatively scheduled a second date for next week. I'm looking forward to it, and I think I prefer her to the first woman. We've got a bit more similar interests and a more of a similar stage of life.
So the questions of etiquette I've been grappling with are things like "when do you stop progressing other potential relationships because of where this one has got to?" and "how open are you about such things?" (the first woman was quite open that I was their second first date of the day when we met up), and so on. I'm really not sure who I can talk to about such things as most people I know in relationships are very much in long term relationships, and I also have such a built in mental image of myself as someone who isn't seeking a relationship that I have a hard time even admitting I'm doing this to other people. Recently someone at work asked who the person who kept coming into the control room to flirt with me was and I pleaded obliviousness despite having considered suggesting something after the project we're working on is completed,
Anyway, these are questions which are kind of difficult to work out a solution from first principles, not least because I don't really know what the first principles are. I've done a bit of online reading, but there's nothing definite. I've seen plenty of examples of what not to do, but that still leaves a lot of possibility space to explore.
I was hoping typing this out might cause something to pop into my head on the matter, but it hasn't and it's late, so I'll wrap up here and commit this to the randoms of the internet, who I feel better about sharing things with than actual friends, which says a lot about me.
