After writing 0.07, I learned of the term, “Aspartame Daddy“, which is far more relevant to my station in life than “Sugar Daddy”.

Florence

Florence and I went out once more on March 24, to Margot Cafe & Bar. The food, cocktails, ambience, and service were all phenomenal. The conversation was light and fun, as she told me about her first week back at teaching and the random crafts she’d been working on in her apartment. The booze and the love she clearly already felt for her students warmed my insides nicely.

The check came. I looked at it, then at her, repeated twice more, then paid after she made no move toward her purse or the check. It was about $250, after tip.

Florence and I had not discussed ahead of time how we would pay for our second date. At our first date, I had told her, “This one’s on me.”

I like paying for the first date. It’s usually just a few drinks and I sincerely appreciate the company of a beautiful and interesting woman. But I try to at least imply the temporary nature of my chivalry. “This one” is not “This one and the next.”

I realized during dinner that I should have been more explicit. I should have said something about splitting the check before I even made our reservation. But alas, I did not, and I felt uncomfortable with springing it on her at the end, believing strongly she would have ordered cheaper drinks and food if she’d been expecting to pay for her share.

It was storming heavily outside, which I used as an excuse to call it a night after dinner. We hugged and she came in for a kiss, which I reciprocated, ever so briefly, before gently pulling away and wishing her a good night.

I have not contacted Florence since.

Angie

I met up with Angie, with whom I’d matched on March 23, at Inglewood Lounge on Sunday, March 26. We had separate checks from the start.

We sat on the patio. It was relatively warm out. She looked stunning and radiated confidence. We talked about neurodivergence, app-building (we’re both startup founders), what’s great and what’s shitty about Tennessee, and the joys of watching reruns of The A-Team.

It was, for the most part, a fun conversation, and I felt a good amount of mutual attraction, but it seemed to me like I couldn’t make a single statement without her contradicting me, maybe like she was negging me.

The most absurd example was after she’d asked what I liked about living in Nashville, I told her, among other things, the food – at which she balked and challenged me to name a single good restaurant.

I named every place I’d been with a date since late January and she relented.

Angie messaged me after our date to tell me she enjoyed it and to give me her in case I’d like to meet up again sometime. I have not contacted her since. As I’m writing this, though, I’m considering it.

Maybe the persistent challenges Angie was hitting me with were coming from a place of insecurity or anxiety and maybe I want to give her another chance. It’s been a little more than a week. That’s kind of a long time, but not too long, I think.

Had you asked me yesterday if I might consider seeing Angie again, I’d have said no, definitively.

So what changed?

Ali

I finally had my second date with Ali last night. She had only been back from Dubai for a day and she was jet-lagged. Conversation was great, but she didn’t seem at all excited to see me.

I tried to chalk Ali’s lack of enthusiasm up to jet-lag, and texted her after to let her know I’d love to see her again next week, after she returns from a trip to California, for which she departs tomorrow.

But my fears were confirmed this afternoon when Ali texted to tell me she didn’t see anything romantic in our future. And so I no longer have a frontrunner, hence the second thoughts about Angie.

Ali and I were all over each other on our first date on March 20. But she couldn’t meet a second time until last night, April 3, putting our second date exactly two weeks after our first. The spark, at least for her, was gone¹.

Moving on

I have a couple new matches on Hinge as of this morning, both of whom interest me as much as anyone else on the app has up to this point. But I am so damn tired of in-app, first date, and second date conversations, especially when everything is scheduled a week or more out from the thing before it.

For example, I was messaging with one of my two new and promising matches, Annie, today. It was going well and I asked if she’d like to meet. She said she’d love to and sent me her mobile number so we could schedule it.

I text her, tell her I’m free almost every night from tonight on, and ask when she’d like to meet up. She picks April 15 – 11 days from today.

Am I supposed to try to carry on a message thread with her until then? Because I really don’t fucking want to. What’s more, Annie’s going on a trip to Rome and Egypt in May, so if there’s going to be a second date and she can’t make it work before that trip then it’ll probably be in June.

It feels like I’m matching with women in my area so we can try things long distance.

I have an idea: I’m going to schedule the first and second dates at the same time with my matches going forward, with the expectation being that we’ll both keep that second date open on our calendars unless we decide to cancel after our first date. If the second date can’t happen within a week of the first, then we won’t do the first yet, if at all. And in the time between the first and second, I’ll try to schedule the third for within a week of the second.

Or maybe that’s too aggressive. Maybe I should just do the first date, ask for a second if it goes well, but then insist that it be within a week or no dice.

I have plenty of matches and I’m sure more on the way. I’ll try as many variations of this idea as I can imagine.

It’s a numbers game.

It’s just a numbers game.

It’s just a mind-fucking, soul-crushing, time-sucking, numbers game.

1. Another detail worth noting here is that I was unable to fill my ADHD medication prescription and so was without meds from March 26 through today. So the version of me that Ali met on March 20 was different from who I was yesterday. I told her as much, but what’s the takeaway supposed to be for her? You’ll really like me except for when there’s a nationwide shortage of Adderall, at which point I’ll be unpredictably either hyperactive or fatigued, as well as frustratingly forgetful, impulsive, inattentive, and suffering from crippling executive dysfunction, until I can get my drugs, which will always be an indeterminable amount of time, but is usually no more than a few days.