Is It Okay To Date My Boss? Ask A Pro

Hi Head Pro. I will try to keep this short.

I’m attracted to my boss. He’s 30, I’m 22. My position is a “stepping stone” position so we both know he won’t be my boss anymore in a matter of months. He has been involved with an employee of his in the past (she still works here, though no longer under him or in his department. She is crazy possessive of him and a potential delusional dater).  There are several things (even beyond the obvious HR issues) inhibiting either of us from making obvious advances. I’ve played drinking games at his house but only limited one-on-one interactions. He seems to make genuine efforts to impress me, but I don’t know if this is a sign he’s interested or just him wanting female attention because attention is fun. I feel like even after I leave this job, he would still feel uncomfortable asking me out due to the age difference and because coworkers would know he was dating a former employee. So: How can I tell if he’s interested when his actions are so inhibited?

Would it be a good idea to tell him I’m interested after I no longer work for him? Or should I wait to see if he asks me out?

Did you know its a bad idea to put “Licks and cuddles,” before your signature on a resume? Also, apparently you shouldn’t sign resumes?

Licks and cuddles,

Office Betch

P.S. I know getting involved with my supervisor is bad idea, let’s just pretend for a moment that it’s not.

Dear Office Betch,

I think you’re doing a little delusional dating and wishful thinking of your own, here. You’re asking a lot of questions and making a lot of assumptions based on the actions of a guy, as you said yourself, you’ve only interacted with on a limited basis (how is that true if he’s your boss, btw?) A 30 year old middle manager is going to be the most insecure guy in any office, because he’s on something of a precipice in terms of his career – of course he’s going to try to impress everyone, especially his subordinates. Men, especially after playing drinking games, aren’t the smartest when it comes to following protocol. I have a feeling, were he interested in you, that he would have made that clear given the opportunity.

It sounds like, as you suggested, that flirting with chicks in the office for attention is just something he does. The fact that there are still issues with his ex-office-fling should be enough to tell you that he doesn’t handle these things well. That said, all bets are technically off once you no longer work there. If you want to put some feelers out there at that time, go for it – the worst he can say is “no.” Again, only once you’re no longer there. I don’t care if you want to “pretend” it’s not a bad idea – it still is. That includes any scenario where you still work there but are no longer under him, btw. Then, you’d be walking into a standard, run of the mill shitty office dalliance, which 90% of the time have standard, run of the mill shitty endings (see: his last office relationship).

Please don’t lick me tho,

Head Pro


I met this guy, and we really hit it off. When we met, we were both just getting out of long term relationships and neither of us wanted anything serious, so those were the pretenses we entered under. However, fast forward three months and I like this guy way more than I initially planned to/thought I ever would. Being a rational, capable adult, I decided to just be upfront and ask him if he thought this could go anywhere. He said that he had hoped I wouldn’t bring it up because he isn’t even sure himself. He leaves for an eight week internship at the end of June (we are at the same college and both stay here for the summers) and says that he doesn’t want to start anything right now because he’ll be gone for so long, but he isn’t ruling it out in the future. He also said “don’t think this doesn’t mean anything because I didn’t think it would be possible for me to have feelings for a girl again”.

I realize that this might not seem all that ambiguous, but the way he put it, it sounded like he was using his internship as a scapegoat for telling me what he actually wanted in the future. Admittance of feelings does not equal a future relationship. I guess my question is, is this going anywhere? Should I broach the subject again when he gets back? I’m one of those girls who likes to protect herself if I’m feeling something that isn’t mutual, and I’d like to get out before I get in too deep with someone who doesn’t feel the same way I do.

Side note: While I realize this is completely juvenile, I can’t resist the urge to ask. His ex is his number one on snapchat so he obviously still talks to her. Should I be worried about that?

Avoiding the Unrequited

Dear Avoiding the Unrequited,

Wait, where’s the scapegoating in this? Sure, you may have selectively inferred that from “the way he put it,” but the fact remains that you still asked him, point-blank, if he wanted this to go anywhere. His answer, as it turns out, was a more or less point-blank “no.” Having feelings for him, it’s totally normal to look for explanations other than the obvious, but you have to face the facts.

If he sounded mush-mouthed, it’s because guys are spineless when it comes to delivering bad news. No one wants to say “sorry, but I’m kind of over this” anymore than you want to hear it. Still, if you don’t buy that, consider other mush-mouthed things he could have said that would have been objectively more hopeful. He could have said “I don’t want to start anything serious right now, but let’s see what happens after my internship.” He even could have said “Long-distance is a bad idea, but this is working right now so let’s at least give it a shot.” But, he didn’t. He didn’t say any of those things. When you asked if it was going anywhere, he said “no,” followed by a bunch of excuses that didn’t really leave many openings.

Still not convinced? Take that last bit, the part about you reminding him that he’s not gay, or whatever. The only time you would tell someone that is following the deliverance of what you believed to be bad news. It’s meant to give closure, to say (literally, in this case) that your time together wasn’t a complete waste. It’s the romantic version of “We will always value the work you did for this company. Please leave your badge with security upon your final exit.”

At least he’s leaving soon,

Head Pro


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