Jay and I connected on Bumble in January of 2019, and met for the first time at a local dive bar in SE Portland at the end of the month for a drink (sadly this Portland institution has since shut down). We eventually confessed to each other and laugh now about how neither of us were looking forward to the date. In fact, I (Cayla) was dreading it! I still remember being at lunch with two girlfriends earlier that day complaining about the fact I had a date with some guy who was very likely to just be like every other guy. But I am pleased to report that we were both pleasantly surprised and spent three hours in easy conversation about all manner of things. I have never been timid on first dates, but I still recall the way Jay made me feel just a little off balance in a good way that evening. When I reflect back, the thing that stood out to me most that night was that Jay seemed very self-possessed in a completely unassuming way, like he knew who he was and who he wasn't, and was very comfortable with that reality. He wasn't putting on airs (which I hate and can smell from a mile away). He was comfortable in his own skin, and made me feel comfortable in mine. I found that very attractive. Given it was a Monday night, somewhere around 10pm we decided we ought to probably call it. We walked out toward our cars, he gave me a semi-awkward hug and then started walking across the street away from me. He half turns and says, "We'll [insert *brief hesitation*] be in touch." I gave him a look like, "Umm, EXCUSE me!? I KNOW you had a great time. We BETTER 'be in touch.'" The next morning I was sitting at my desk and decided I had nothing to lose. I was going to be my direct self and reach out to him. I sent him a message telling him I had enjoyed our date, but that our goodbye had confused me a little. I listed the things I liked and found attractive about him and gave him my phone number, but told him to only reach out if he was actually interested in continuing to get to know me because I wasn't interested in a pity second date. About 5-minutes later I got a text from him saying, "Hi Cayla, it's Jay :)" And that was that. We had a second date, and 2 weeks later, on a lazy Sunday afternoon he told me, "I think I'd like to call you my girlfriend," at which point I think I just laughed at his cheesiness. He has since upgraded that title ;)