Dear Prudence

Dear Prudence Uncensored: The Colleague Crush

Every week, Danny Ortberg and Nicole Cliffe discuss a Prudie letter. This week: the letter writer in an open relationship who wants to ask a former colleague on a date.

Danny: i’m taking us both out of our comfort zones today!

i feel like whenever i do “open relationship” questions, 9 times out of 10 my answer is “this is a really bad way to try to open up a relationship, just break up” so i’m trying to branch out


Nicole: Right!! This seems like a stable, healthy open relationship and people so rarely write in about those!

A of all, congratulations on smoothly transitioning to an open relationship

Danny: yes! well done you!

Nicole: B of all, do you still work at the same PLACE with this gentleman?


Danny: obviously my strongest inclination is to say: Look, if you don’t know how he’s going to react, and he works in your field/sometimes with your company, do not tell him you’re in an open relationship, because what if it backfires


like, is he a freelancer who often works for your company? is he in the same building?

Nicole: I definitely think those details are relevant


Danny: is this a total one-off and he’ll never work with you or any of your colleagues ever again?

right, I really don’t want you to ask this guy out and then have him react badly and maybe gossip about you at work

Nicole: Exactly

I might go with a light email about being interested in getting to know him outside of work

Danny: in general I think it’s a good idea to keep work and romance separate unless it’s completely unavoidable, so even if that means occasionally letting a cute sort-of-colleague pass you by, that’s your best choice

Nicole: and then IN PERSON you can be clear

yep, agreed if colleague


also I married someone from work but agree completely with you


Danny: that was completely unavoidable!!!

you had a CHASTE COURTSHIP and then before Steve WENT AWAY TO EUROPE he said “i think we should either stop being friends or become very seriously involved and probably married”

that was some “stop the world i want to get off (and move to the mountains and have babies)” stuff

Nicole: It was very very beautiful and moving

Danny: so I think maybe the best move now is to talk to your partner about it

since this exact situation has never come up before

Nicole: That’s a good idea

Danny: and you two might want to have a sort of official policy


on how you deal with attraction or infatuations that come up at work or through work-adjacent things

Nicole: Also please watch the Chris Fleming video about polyamory and don’t do any of that

Danny: yeah don’t invite him over for board games and “announcements”

but I don’t get that vibe from this LW

Nicole: Not at all.

Danny: so have a preliminary talk with your partner about work-related people, think about possible worst-case scenarios and whether you think it’s worth the risk

Nicole: So, yes, if they are not really your colleague, ask to hang out outside of work and then be clear and polite and prepared to back off


Danny: if you decide that it is, and you’re prepared for it to become uncomfortable or awkward, then I think you can try to gauge his interest obliquely


Nicole: if they are, think carefully and talk to partner either way

Danny: yes

and you know, I’m all about self-preservation, so I think it would be fine to just get together and try to raise the issue indirectly to give him a chance to signal what his interest level in open relationships is

Nicole: scripting for “I am in an open relationship” when you DO want to explore becoming romantically involved is tricky

Danny: I would honestly be a little cheesy and labored and try to bring up the IDEA of open relationships using the specter of “a friend” for plausible deniability

just in case his reaction is, like, “Oh God, never”

Nicole: “And since I’m in an open relationship myself, I tried to help her…”



Danny: I feel like a spy, this is great

Nicole: also you are so into making up a friend

which I love



Nicole: I agree!

ok I did get called on it once


Danny: “my friend…..she doesn’t go here…..she has nine boyfriends, they all live on the moon”


Nicole: it was in college

Danny: who would dare! you have to let people have the polite fiction of the friend!

Nicole: called me on it WHERE I STOOD

in real time

Danny: I am so, so sorry

Nicole: I hope he’s not her colleague and they have a nice time and maybe date


Danny: but in sum: I think the reason you’re finding it so hard to come up with a good script and are worried he might feel misled is because it’s very difficult to bring up your open relationship in order to hit on a former colleague, which is probably a good thing, because I think work should mostly be for work and looking for prospective partners should be its own thing

Nicole: RIGHT


Danny: if in this particular instance the guy is open to the idea, he’ll definitely let you know once you kind of heavily hint at it

if he doesn’t, back way off

and look for cute guys outside of work


Danny: there are worse things than having periodic crushes on people you encounter at work and just sort of releasing them back into the world

non-consummated crushes are perfectly nice

Nicole: That’s honestly so true

Danny: *joyce from buffy voice* have you tried NOT consummating your work crushes