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There are strict rules for him at work

Is that why he hasn’t asked me out?

Love Letters

Love Letters

Q. I really like this guy I met at work.

He only comes in once a week and works with our residents at a rehabilitation and nursing home as a licensed clinical social worker. He has positions at a few other places and works a significant amount of hours.

We have clicked during our conversations while on the clock, and I feel a unique kind of joy, peace, and magnetic connection around him. When I’m in his presence, we are both smiling, laughing, and making jokes. It feels natural.

However, I don’t see him at work much these days, and he has yet to ask me out for coffee or to meet up outside of work.


His position does have strict boundaries between other colleagues, so I’m wondering if that’s why things have not progressed. I don’t want to force anything if it’s not there, but I feel like he is interested and I’m interested. What should I do?


A. If there are strict rules at work, he might not want to risk any of this. At the very least, he won’t want to initiate.

My answer, for most work crushes, is to start small — and in a group. Coffee alone might be too much like a date. You’re better off inviting him out with colleagues. See if you can gather friends to spend time at a restaurant after work so he can join you. And sit next to you. And maybe more.

He might say no — or maybe he’ll be too busy — and at that point, leave it be. You’ll have shown your interest and he can make the next move if he wants to.

Please don’t get your hopes up. He might interested, or maybe he’s a personable guy who connects with you as a peer. Don’t overthink it or build it up too much. Plan an outing, and if he says no (with no follow-up), enjoy him at work and move on.




“You’re better off inviting him out with colleagues.” Only if the colleagues go out together with any sort of regularity. Otherwise, everyone will sniff out what’s going on here, right away.


Let him know you’re interested in being asked out. Something casual like, “I always look forward to seeing you at work. If you’d like to hang out some time, let me know.” Don’t try to figure out his world. Let him figure out if dating you could create problems for him — or if he’s sufficiently interested in you.


^Yes. Let him know you’re available and interested, but don’t clobber him over the head with it.


I work with lots of attractive women. They are polite, personable, and cordial. We make small talk, we tell safe jokes to each other. However, they usually have a spouse/partner at home. They’re usually not interested in dating anyone at work. He is probably just a nice guy who is already taken.


I’d like to know more about the strict boundaries between other colleagues. I can see not dating his patients, but who would really care if he dated a [colleague]? Although in general, dating someone at work can get awkward if people break up. Lucky for me (?), there’s no one at my workplace that would be remotely interesting to date.



The thing is, in your imagination you can think about him as a potential relationship blossoming into a life partner. But “someone who makes me laugh and feel at ease” isn’t worth risking your career over. That’s all this is at the moment, if it’s even that. There are other guys out there.


Why would you want to get involved with someone who has no time for you?


Move along and look for someone outside of work. We all know work crushes come and go.


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