The Alum pops up on Facebook chat. He wants to know if I have a smartphone with a data plan.

Yes, why? I say.

He wants to share a playlist he made on Rhapsody. It’s an 80′s playlist, an awesome one.

To be polite, I tell him I’d love to hear it – but I don’t have Rhapsody.

A few minutes later, a Rhapsody gift subscription code arrives in my inbox, along with another email containing a link to his playlist.

I’ve done a lot of reading on how you know when men are interested, and here’s one way: they send you a mix tape.

Or, as it happens, a really awesomely long playlist of every song I avoided listening to in high school.

I don’t dig top 40 music – never did. I don’t mind it – I have some Michael Jackson and what have you – but I was always the “obscure English art band” type. I can tell you the names of every band that was on the 4AD label until 1992, without the aid of Google.

You may not be impressed with that and you’re welcome to think my music is pretentious crap –  but you should probably know that before you send me the soundtrack to my worst high school nightmare.

I feel guilty and I feel mean. I wish he hadn’t spent the money and I definitely wish he hadn’t created the playlist for me. I tell myself it’s possible he didn’t make it just on my account, but I don’t believe me.

I avoid him for a couple of days, but then he pops up one day, asking what did I think. I’m having some fun with Rhapsody, I tell him in an effort to be positive and yet truthful. I spent a little time building a playlist of current music I like (Gorillaz, Lindsey Stirling), which is kind of fun.

He asks if I like the playlist and I say I lost the link somehow. He resends it.

I see the problem with technology in dating: he cannot hear the guilt and awkwardness in my replies; he cannot read between the lines, though perhaps he just chooses not to. But without the other cues available, working only with pixels on a screen, it’s easy to fall into this trap.

A day or so go by, and he messages me again. He’s added some Bananarama, he says, because he forgot it originally. He’s thorough; he’s included everything.

Every detail.

I want to tell him that Bananarama originally sang backup for a band called Fun Boy Three, and that was a really good band. But he’s not asking for a conversation, nor is he trying to get to know me. He wants a gold star.

But I don’t want to give him one: he submitted a lot of data, but entirely missed the point.

The day after our date, The Alum messages me on Facebook. He sends me a link to a product he thinks would be nice for The Child for Christmas, and a link to the pizza place we talked about.

I can’t decide how to reply, so it takes me two days to get back to him.

I don’t think that’s good, and I’m pretty sure he knows that, based on the tone of his replies.

A few days later, he posts an article in the Alumni Facebook group I run that almost no one uses.

A few days after that, he texts me asking for the name and email address of another alumni in the area that he met at our summer picnic. It takes me a while to reply, mostly because the request is on my phone and the information is on my computer and I need both to be in the same place at the same time as I think of it.

A few days later, he messages me on Facebook with the same question.

Oh, I say, so sorry, I meant to reply. I’ll check now.

He messages back while I look it up: It’s not urgent, he says. I want the name of the place he got the dumplings he brought. They were very good.

Finally, I arrive at the restaurant. The Alum wants to order a bottle of wine, but that seems like too much of a commitment, so I demur and say I prefer mixed drinks. I have no idea what mixed drink to order, so I chat with the bartender for a bit in an effort to decide. He asks me what TV shows I like and I say Mad Men, so he brings me a Sidecar. It’s Retro, the bartender says. You’ll like it.

The place is busy, noisy. I can mostly hear The Alum, but not entirely. We chat first about my divorce. I don’t get into the details, providing just the minimum information. He listens to the facts, and seems to file them away, not asking too much, just listening.

He tells me about his new job. He found the job through a personal referral, and is very happy there. He tells me about the interview process.

Every detail.

I order another drink, and though I liked The Sidecar, it’s making me fantasize about Don Draper, so I ask the bartender to surprise me with something different. He makes something up on the spot, involving a mix of things I wish I’d asked him to write down, because it was good and I could not hear what he said was in it over the din.

The Alum and I  move on to other topics. We’re probably due for another alumni event, so I ask if he has suggestions, knowing he will. He suggests a pizza place that is supposed to be really good. I don’t doubt that he’s right:  he’s from New York, and New Yorkers know pizza.

It is also possibly the least-conveniently located place I imagine. But he says it’s worth the trip, and tells me about it to persuade me: It has old pinball and Donkey Kong machines. He tells me the story of how he found the place the first time – off the beaten track as it is. He tells me everything about it.

Every detail.

It’s not an unpleasant conversation, but it’s becoming a long one. It feels a bit like a math test where you’ve been told to show your work. I wouldn’t mind that, but the subject matter feels like it’s more suited to a multiple choice test.

Bubble in, I think.

It’s becoming late and there’s no obvious point of exit. Everything I say prompts a response, a story, even if it’s a remark that is clearly intended to wind things down. But  I can’t be out all night – even on a weekend, which it isn’t.

I finally get up rather abruptly, and say, Thanks so much, but I have to go home to my child, she has school tomorrow.

He seems disappointed, but insists on picking up the check. He lingers at the bar and since I realize it will take a very long time to actually exit with him, I decide to exit alone.

It feels rude, but it also feels like a boundary, and that’s the thought I savor as I drive home, carefully avoiding the fake snow and manic, dancing nutcrackers.