- Wedding: June 2019 - Tacoma, WA
My most embarassing date story, off the top of my head, was the time I literally didn’t realize I was on a date until much later than I’m proud to admit.
I knew this person as part of a wider friend circle. So, we weren’t close friends by any means, but we knew who each other was by name and chatted occasionally if we happened to meet up at an event or larger hangout, etc. Anyway, one night she suggests we go grab dinner and drinks sometime, and I agree. This was after we had chatted at a bar one night when a bunch of us were all hanging out, and our convo was interesting, so I just thought of it as a “let’s continue this conversation over dinner and drinks sometime!” But, apparently, she liked me and was asking me on a date.
A few important facts to know: One is that I’m the kind of person who has to be told outright if someone is interested in me, or I will literally never think that’s the case. I don’t pick up on hints or cues. I always just assume people are being friendly. Second, is that in the lesbian dating world, it really can be hard to know what’s a date and what’s just hanging out as friends. And, third, this person was super sweet, but was not someone I was attracted to on any kind of romantic/sexual level.
Ok, so the evening comes around and she picks me up at my place to take me to dinner. Parking in my city is rough, so when she offered to pick me up, I figured it was a good way for us to only need to park one vehicle. When we talked about doing dinner and drinks, I told her to pick a spot, so she did – a fancy place overlooking the water. First we stopped at a local bar for a few drinks, then we walked over to the restaurant. She paid for the drinks, which I thought was nice, but didn’t think much of it. I was seriously nervous about the restaurant, though, because it was quite a bit outside my budget, but then, I HAD told her to pick a spot and I didn’t want to disclose my lack of funds, so I just kept quiet and did frantic math/budgeting in my head while we walked. She opened every door for me, which I thought was sweet, but again, didn’t really think much of it. I open doors for friends all the time.
We get inside and she’s made reservations for a specific table at a window. The view is obscenely beautiful. We order some drinks and start looking at the menu and she asks me what I think looks good. I’m looking for the cheapest thing on the menu when she suggests a somewhat expensive dish she loves and insists that I “have to try it” so I go ahead and order that (it did look really good), while panicking still in my head about what this is going to cost me.
We enjoy dinner and a couple of drinks and have a lovely conversation. She’s asking me about what I do for work, about my family, what my passions are, etc., the kind of stuff you ask someone, oh, I don’t know…ON A FIRST DATE…but I’m oblivious still. The check comes and I politely ask the waiter to split it, but she takes the check and kind of smirks and says “you’re so sweet, but I’ve got this” and pays the check.
After dinner, we continue our conversation as we walk along the waterfront back to her car. She’s telling me what a great time she’s having and that she hopes we can do this again soon and how hard it is to meet people she really ‘connects with.” I agree we should do it again soon, tell her I’ve also had a lovely time, and she moves and proceeds to give me the most awkward hug of my life. Looking back, it’s clear she was trying to kiss me but I made the hug move instead so she rolled with it.
She drives me back home and walks to my door with me. Cue a few awkward moments outside my door where she’s just kind of looking at me with this expectant look on her face as we make smalltalk, like she would like to hang out longer, but I’m kind of exhausted at this point and it’s super late and I’m not really feeling up to hanging out even later (because I still for some reason think this was just a friendly hangout with a new friend), so I thank her for the lovely evening and tell her next time drinks and dinner are on me, give her another awkward non-kiss hug move and say goodnight.
Ya’ll, it wasn’t until I was telling a mutual friend a few days later about our hangout and what a good time we had that I finally understood – when she said “Dude, you do realize that was a date, right? She’s been into you forever and finally had the courage to ask you out!”
Looking back on the evening, it was pretty freaking clear, but apparently not to me. I was so embarassed that I hadn’t picked up on all the cues that I couldn’t even face her again for the longest time afterward.
Years later and we’re fairly good friends now, and we still laugh about that time we went on a date that I didn’t even know was a date until literally days later.