Dear Prudence

Dear Prudence Uncensored: Help! I Set up a Co-Worker and a Friend on a Blind Date. Her Drink Order Ruined Everything.

Each week, Prudie discusses a tricky letter with a colleague or friend, just for Slate Plus members. This week Jenée Desmond-Harris discusses her response to “Dairy Disorder” with fellow Slate writer (and also her husband) Joel Anderson.

Dear Prudence,

I (a married woman) just set up a single male co-worker and a single female friend of mine on a blind date. He’s a sharp guy who’s traveled the world and knows all about fine foods, wines, classical music, designer labels, etc., and she’s a stunningly beautiful and intelligent artist. I really thought they’d make a great couple. Immediately after their date, my friend thought it had gone well and was very excited. On Monday morning, I asked my co-worker, and he said my friend was attractive and a nice person, but he wouldn’t be asking for a second date.

My friend has been bewildered by her difficulty in finding a steady relationship, so I pressed him as to why. He told me they went to a swanky bar, and she—wait for it—ordered a plain glass of milk. He found this so clueless and childish that he couldn’t imagine being with her. Now my friend is neither a big drinker nor a teetotaler—just someone who’s going to order what she wants without worrying about what others think. Should I tell her why she won’t be hearing from this guy again, so she can reconsider ordering milk on dates in the future? Should I tell him how ridiculous he is for judging someone for something so petty?

—Dairy Disorder

Read Prudie’s original response to this letter.

Jenée Desmond-Harris: This was funny to me because I just recently told you to “stop being a child” and trade your beloved energy drinks for coffee. I stand by it.

Joel Anderson: We don’t have to go too deep here, but you’ve also previously criticized men for ordering hot chocolate on coffee dates. You’ve clearly got some very problematic views of what constitutes maturity and we don’t have enough time here to get to the bottom of it! But this demands follow-up at some point.

Jenée: Connecting it back to the issue at hand. I do have strong opinions about beverages but here’s my thing: If you really like a person, you’ll let it go.

You drink chocolate milk and don’t like coffee—all things that have inspired me to accuse people of being 5-year-olds in the past—and barely consume alcohol and I still married you! So this single male co-worker simply didn’t like the letter writer’s single friend enough.

Joel: Thanks for tolerating my (apparently) childish choices of beverage. Also, I don’t hold your coffee addiction against you. That’s very fortunate for both of us because I think we’re mostly enjoying this relationship lol. But to your point, if this was someone the LW’s co-worker was really into, ordering a glass of milk at the bar would be a cute little quirk they tell their family friends about someday.

Jenée: Exactly. So no need for LW to intervene.

Joel: Right. I mean, it’s totally fair for the co-worker to say, “This is weird and I want no part of it.” But let him tell the LW’s friend why he’s not going to ask for a second date. That’s the least he can do under these circumstances. Because once someone accepts a hook-up from a friend, then they need to be responsible enough to manage the fallout.

Jenée: That’s such a good point. A much bigger issue than the milk question. And LW should take a more hands-off approach to hookups. You’re a connector, not a dating coach.

Joel: Oh yeah. I mean, in some ways, it seems like the LW also had fairly shallow reasons for hooking them up. She talked about how attractive they were and hinted at their mutual sophistication, but that’s not nearly enough to stoke those internal fires. There are good looking people everywhere. Whether you actually want to date them involves a whole lot of variables, which include things like, “Please don’t order milk on our date, ma’am.”

Jenée: Right: “Knows about designer labels.” Okay so does every 19-year-old on TikTok. Dig a little deeper here.

Joel: Also! Don’t tell your co-worker that he’s being ridiculous. He gets to decide what matters under these circumstances. Hell, we could even dig a little deeper into whether it’s even professionally appropriate to be wrangling co-workers into these sorts of situations. But that’s beside the point: Please don’t confront him, unless he’s just deciding to ghost your friend. At that point, maybe nudge him to follow up. But a hands-off approach here seems to be the best policy.

Jenée: And rest assured that the right person will love your beautiful friend and her toddler-like beverage preferences.