Still have that crush on my boss

Wednesday | October 2, 2024

Love Letters Dating

Still have that crush on my boss

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Hi Meredith,

Wrote to you many months ago (maybe even a year) about a flirty relationship with one of my female managers at work. We are very different, including our age and race. I’m significantly older.

At the time, when I previously wrote to you, I just couldn’t seem to break through any of these differences to ignite any romantic interest from her. I tried and tried – we chatted and gabbled – but it was just a continuous cycle of innocent flirting.

Well, I recently returned to work from a month-long summer vacation and she came sprinting to me with an enormous embracing hug. We held each other for a quick while then separated and chatted for what seemed like an eternity. And the flirting started all over again!

I know it’s awkward and probably against company rules to date your boss but do you think I should try again to pursue this relationship? If so, how do I get past the flirting to something more substantive?

– Still Flirting

It’s time to let this go.

I mean, I told you that before. Things haven’t changed.

She hasn’t taken it past friendship. She hasn’t seemed interested in quality time with you outside of work. Also, she’s your boss – which means her job is on the line. If one of you left the company, that might open doors, but you’re both still working there.

You mention the hug, as if that’s a game-changer. Some people are big huggers, some are not. You’re looking for signs here, but I don’t see any.

The only thing you could do – to clear your brain of this – is to ask another manager (or HR) about the company policy on asking someone out on a date. Find out what the rules are – and if you can report to another manager.

If it’s OK to express interest in someone who doesn’t work for you, and you don’t report directly to them, you could suggest plans to this woman once, or hand over your number and say, “If you ever want to go on a date, let me know.”

But honestly, is it worth all of that? I’m not so sure.

It sounds like you could use more time being social outside of work. The month-long vacation sounds great. Maybe new hobbies and social groups would also help.

– Meredith

Readers? How can this LW let go of the idea of dating this person? What is this about?

I’d love to read your question. What’s on your mind about being single? Dating? Breaking up? Send your own letter by using the anonymous form or email [email protected].

Office Crush