[fpeezy]

I’ve been in a complicated situation for a little over a year now. I’ve been crazy about my manager, but I never knew how to handle the situation. I’ve wanted to ask him out for the longest time without weirding him out. It finally got to the point where I gave up and decided it made no sense to like him. Then a few months ago, he noticed that I didn’t act the same and thought I was upset. I’ve been having a hard time in my life, so of course it made me like him again since he noticed that I wasn’t the same towards him.

Recently, he had told me that he wished I went to a party where only managers were invited. He said, “I’m okay with hanging outside of work with you because you’re you, but any other employee wouldn’t be okay”. I don’t know what to do. I’m contemplating talking to his roommate because him and I are friends. I’m stuck between talking to him about my manager or just somehow asking my manager to hang out. How should I go about this situation the best and least awkward way?

[AskApril Masini]

Why not flirt with him a little bit? Find opportunities outside of work to flirt with him a little bit more, without jeopardizing your career or your job or your work, and let him know you’re interested in him beyond what he already thinks. It sounds like he’s looking for a clue or a hint from you that there’s something worth chasing after.

The best way to really turn up the heat is outside of the office — especially if there are situations where people from your workplace might go for a drink after work, or a gym where a lot of people go, or a place where they eat lunch or grab coffee. In other words, you have to work a little harder at creating romance and flirtation, but it’s the best way for you to change the dynamic you’re in. 😀

[Member]

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