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It was pretty one-sided, as I was trying to maintain the professional boundary.

The breaking point came when he sent me a very long text one evening, which was incredibly inappropriate.

Things got more normal at work and I though the issue was resolved.

However, he came to my office a couple of weeks after the text incident and asked to have my number back! Later that week, he IM’d me and asked if I had thought anymore about his request.

When I tried to pull back to a more professional relationship, he thought I was mad and bought me a candle (I mentioned once in a conversation that I like candles).

When I still “seemed mad,” despite repeatedly telling him that I was not, he asked me to lunch and tried to have a heart-to-heart type conversation.

You made me really uncomfortable with some of our previous interactions, and I don’t feel comfortable having a social relationship with you.” But really, good for you for clearly telling him to back off.

So often in these situations, people worry about being polite or hurting someone’s feelings or causing tension in a work relationship and so they end up accommodating increasingly inappropriate behavior.

In general I’d default to HR for harassment issues because they’re trained to handle them in a way managers often aren’t, and they’re more likely to know if there have been other reports of problems with this guy.

I replied and said that my answer hadn’t changed and that I would just like to remain work friends.

Since then he hasn’t done anything majorly out there, but he does continue to talk to me about non-work related things (what are you up to this weekend? ) that from anyone else would be normal but with his history of crossing professional boundaries makes me uncomfortable.

But anyone looking at what’s happened here is going to understand that that’s a likely subtext, and no reasonable employer is going to want an older male employee hassling a young female employee for her phone number after she’s already told him no.

(They shouldn’t want it if the ages were different either, but this lines up so closely with a common problematic pattern that they’re not likely to miss it.) So you’re on solid ground in talking to your employer about this.

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