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I made some mistakes in my friendship with a co-worker who I will call Jane. Although I am in committed relationship and I told her that, we both have not really brought it up too much since then. It is nice to have someone to talk to at work and if I am beginning honest, things in my relationship have been a bit stale — my girlfriend works long hours as well.
I have been sort of toeing the line with Jane and although I really do like her, I don't want to break up with my girlfriend. Is there anyway to reestablish boundaries? (Nothing physical has happening, although we have come close.)
Jane does not sound much like an innocent party either. She knew you were in a relationship and that was probably part of the reason the two of you became so close. There are so many different ways two people can derive sustenance with each other. The kind you have chosen is essentially unhealthy, since it lacks real intimacy with either party, but maybe that is just the sort of arrangement you prefer.
The real problem is in your primary relationship. Maybe you don't want to be with someone who works such long hours. Normally I would advocate a fresh lie, but telling everyone involved the truth is most likely going to lead to your best result. Half relationships can sometimes become full relationships, and it is possible either of these situations might be repaired to your satisfaction.
It is always disgusting or skeezy to ask someone who you met while they are working? I have built up rapport with an administrator who is employed at a hotel I often visit for work. I don't want to make her uncomfortable by hitting on her, but there must be some way of letting her know I am really interested.
She has to deal with this a lot in her job. Building "rapport" as you call it is really just an aspect of service jobs. You're a client and thus you receive this treatment because you have paid to receive it. It is really no indication of romantic interest on her part.
It is OK to drop hints, but never intrude on her private space or well-being. If she really picks up on what you are broadcasting, maybe it is then OK to straightforwardly ask if something more is going on. Without that green-light, you are just being a dick.
Illustrations by Mia Nguyen.