The Luv Doc: One-Percenters

Dear Luv Doc,

Over the last two years I have become really good friends with one of my co-workers. We work in the same building but are in completely different divisions and we mainly talk over lunch in the break room. Over the time I have gotten to know her she has shared a lot with me about her marriage, children, and friends. We share a lot of interests, and we even have some of the same friends at work. Recently she told me she just finalized her divorce and her husband moved out of their house for good. For this whole time I have been romantically attracted to her, but never said anything because she has been married and I am quite a bit older than her (I’m 56 and she is 37). My gut tells me that if I don’t tell her how I feel now, I will miss an opportunity because recently she has been complaining about having to go on dating sites again. I just worry that she might be creeped out because I am old enough to be her father, and although we have shared a lot of really personal things, I am not sure if she is into me romantically. How do I tell her about my feelings without seeming like a lecherous old man?

– Old Guy in the Break Room

I think if you’re truly intent on letting this woman know you’re romantically interested in her, you might need to make peace with the idea of being seen as a lecherous old man. Statistically, the chance of you two hooking up is pretty remote – like 1 in 100 remote. To put that in perspective, you have an equal chance of developing an aneurysm. Some people might look at those odds and think they should start scouting up a good neurologist. Strangely, those people are called one-percenters. 

Why? Because one-percenters are the only people who can afford PPOs and, correspondingly, get to choose their medical specialists. You’re probably going to need to summon a one-percenter’s optimism to confidently make your case. However, before you start picking out romantic restaurants and composing love sonnets, please allow me to take a swing at playing devil’s advocate. After all, so few people advocate for the devil these days – except for maybe that satanic doo-wop band Charley Crockett kicked off his tour. In Charley’s defense though, it’s entirely possible they didn’t like Hank Williams.

It’s also entirely possible your at-work ingenue knows all about Twin Temple and nothing about Hank Williams. If not, there will surely be plenty of other generational impasses. What if she thinks Red Hot Chili Peppers and Nirvana are just mid? What if you say “take me to the place I love” and she doesn’t respond with “take me all the way?” What if she doesn’t know that a mulatto and an albino are followed by a mosquito? What if … and there is at least a 1% chance that this has already happened … she calls you a boomer when you’re so clearly Gen X? Them’s fighting words – even if you do own a Beatles boxed set. I mean, doesn’t everybody?

Along with your boomer leanings, there’s also another sticky wicket: You have been chatting up this gal in the break room for two years, talking about personal stuff, and you have no idea whether she’s into you romantically? I really can’t imagine a surer sign she’s not. She just came off a divorce and instead of telling you she has a weird fetish for gray pubic hair, she complains about having to go on dating sites? Bruh … as the Gen Xers like to say (when they really want to annoy their children), that shit is mad sus.

However, far be it from me to stand in the way of true love, even if that true love could potentially make your friendship with this woman insanely awkward and even jeopardize your job security. So, do what you must, but maybe instead of unexpectedly gushing out your innards, you could start small … test the waters, so to speak. Ask her if she would be interested in dating an older man like yourself. If she’s a 99-percenter, you can just laugh it off and maybe still be friends. Tread lightly though, and don’t be a sore loser.

This article appears in August 7 • 2026.