Should I [M] ask my coworker [F] out knowing that a relationship could not work out?

So I've been debating on asking out one of my colleagues for a few months now, we work in different departments but when we do see each other around the office the connection is obvious. The flirting is clear and mutual. Her vibe is great and I know we would have a lot of fun together but there are a few reasons why I haven't made the move yet. (Aside from the obvious reasons not to date coworkers)

She is about 5 years older than me and is a single mother. I don't see myself having a problem with her having a kid and obviously putting her child first, however I am still in my early 20's and have never dated anyone older or anyone with children.

I have dated coworkers in the past and although it didn't work out, there was no real negative outcomes. We just decided to go back to being normal coworkers and there was no drama. I just feel this one is different.

I'm hoping some of you guys have experience with a situation like this and could chime in with some advice, TIA.



Submitted August 27, 2019 at 11:24PM

So I've been debating on asking out one of my colleagues for a few months now, we work in different departments but when we do see each other around the office the connection is obvious. The flirting is clear and mutual. Her vibe is great and I know we would have a lot of fun together but there are a few reasons why I haven't made the move yet. (Aside from the obvious reasons not to date coworkers)She is about 5 years older than me and is a single mother. I don't see myself having a problem with her having a kid and obviously putting her child first, however I am still in my early 20's and have never dated anyone older or anyone with children.I have dated coworkers in the past and although it didn't work out, there was no real negative outcomes. We just decided to go back to being normal coworkers and there was no drama. I just feel this one is different.I'm hoping some of you guys have experience with a situation like this and could chime in with some advice, TIA.
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