This is a little embarrassing given the age difference, but I have this internal conflict within me where I feel a certain way when I talk to this specific colleague of mine and to be honest I’m not really sure how to handle it.

I know that there are a couple red flags to begin with -mainly the age gap- and the fact that she’s my colleague but I can’t seem to get rid of the feeling. The fact that she’s a co-worker isn’t much of an issue as she works from home whereas I work from the office on most days, and we’re rarely actually forced to interact for more than a couple of messages at a time. But I know that the age difference is weird and is the bigger issue, although I must state that she has in-fact not done anything specifically to ‘groom’ me or to make me feel this way, it has stemmed from our natural interactions throughout my time of working at my current place.

I have admitted to myself that I find her very attractive physically, and she is also the nicest person you can talk to at the office but she’s just generally nice to everyone. I don’t believe that she is interested in me other than for work purposes but this is where my dilemma comes in.

I’m not sure whether I should act on how I feel and perhaps try to make some small talk unrelated to work or if I should leave it and keep it strictly work related. I know that common sense would dictate the latter, but it actually is kind of difficult for me when for whatever reason she’s physically in the office. And I’m also aware from her point of view, how it would look like if anything was to come from it, I think people would definitely be weirded out if they found out. Even if she rejected me that would give me some kind of closure, but given the nature of our relationship I can’t just ask her straight up.

Any advice is appreciated

2 comments
  1. I am actually going to ignore the age gap for a moment because honestly, OP, you shouldn’t be trying to hook up with someone you work with, regardless of age. I know you say she works from home, you work in the office, etc, and you seem to think this is why this is something you could go after. I do not advise it.

    Now, about the age, I am 35 and I can’t imagine being with anybody your age. If someone who was 20 approached me I would probably be flattered but ultimately I wouldn’t go there. Saying that, yes, I am five years younger (or more!) than this woman. You two will have nothing in common. She could genuinely have a child your age.

    Just don’t try it, full stop. It’s a bad idea.

  2. Don’t hit on people at the workplace. There’s far more risk than potential reward, and in this case it’s a totally cold “shoot your shot” moment that just isn’t appropriate in this setting.

    Now, can you at twenty find women who are forty attractive and enter into an ethical relationship? Yes.

    Set your age on the apps higher and find yourself an older partner.

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