We’ve (29M, 27F) worked together for about three years, though not very much directly. I know a fair bit about her, we’ve spoken in bits and pieces over the years, shared laughs frequently. I’m not sure if there’s any real deep connection waiting to be uncovered, but I’m very attracted to her. How do I approach the situation in a way that doesn’t make her feel uncomfortable, but opens the possibility of dating? Thanks in advance.

3 comments
  1. Mate… It’s taken you three years to even consider this?

    Have you reviewed your workplace policies on workplace relationships?

    Do you really want to make things awkward if they don’t work out?

    Leave her alone and let her work.

    If she was interested, you would know.

    You shouldn’t need advice if you’ve known her for 3 years… The people on the internet know nothing about you 2.

  2. Dangerous territory. I’ve been asked out by female coworkers (I’m a divorced middle aged man), but asking out a woman is tricky. The rule is once. When it doesn’t work, it gets weird. You had better be ready for every female coworker to know your actions and words.

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