Love Letters: Should You Pursue Your Workplace Crush?


It’s been awhile since I’ve pulled out the mailbag and dug through a few Love Letters. No better time than the present to catch up.

Need some advice on your relationship? I’ll happily butt in your business. Here’s how.

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Here’s today’s question:

I have a workplace crush. I know he has a “female friend” that is not his girlfriend. He says he doesn’t mess with women in the workplace. I can dig it but we are always having intellectual conversations, we have a good vibe. I catch him staring at me and he has told a fellow co-worker that I’m beautiful and if he didn’t have his female friend and didn’t work with me he would holler. I know he likes me. Should I just keep being his friend and try to break him down or just take an L on this situation?


Now, typically this is the time where I’d warn you of the dangers of workplace romances but y’all know I’m realer than Real Deal Holyfield, so I have to keep it authentic.

Workplace romances CAN work.

Emphasis on CAN.

I’ve had workplace romances end up like this on a couple of occasions:


But my final workplace romance wound up like this:


So I’d say things worked out.

Now before you open up that David’s Bridal credit account, chill for a second – let’s think this through.

Strike 1: Dude already said he doesn’t want a workplace relationship. And I can’t blame him there. While it’s natural to form bonds – and attractions  – with people you spend 40-something hours a week with, the downside is you spend 40-something hours a week with them. Unless there is a real connection there, those cute crushes can become irritating real quick.

Lord help you if you sit near them and they crunch on chips all day. Ugh.


Strike 2: Dude said he doesn’t want a workplace relationship but tells another coworker that IF HE DID, you could get the business.

Playa please.

Ladies, sometimes you underestimate how well men scheme. I’m willing to bet my Keith Sweat CD collection that this third-party coworker is a friend of yours. There’s no way your crush would bare his soul to the random guy who can never figure out how to unjam the printer.  He told your friend that info knowing that it would get back to you. That way you’ll hang on to a glimmer of hope that somehow, maybe, you’ll have a shot with him.

This is middle school stuff.

Strike 3: He has a ‘female friend.’ Not a girlfriend, but a ‘female friend.’ Question: Does this woman know she’s just his ‘female friend’ and not his girlfriend? Don’t get caught up, sistas ain’t playing in these streets.


Look, it’s obvious that this guy likes you but there’s way too much double-talk and uncertainty going on to pursue a real relationship. By all means, continue being friends but when it comes to dating him, this brother has already used up his three strikes. Be out.

Sorry, you’re taking an L on this one.



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