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TherapistJen, LCSW, CPC
Category: Relationship
Satisfied Customers: 3204
Experience:  Licensed Clinical Social Worker
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I want to date a girl from work, but she's very confusing.

Customer Question

I want to date a girl from work, but she's very confusing. I know she's single.
She started recently. In her first days of the job, we went to a tour together for a tradeshow. During these two days, we went out to dinners, drank wine, had great conversation, but I tried to stay away because I'm her boss, and I didn't know her enough. I don't know if these would be considered dates, I thought they weren't, but we did talk about dates, her friends' weddings she told me she's very liberal etc. Would these be considered dates or just professional dinners (because we both had nobody else there)? I'm not American, so I don't know the culture here very well.
My second question; after that I asked her for a dinner, added "I don't want to bother her" She said it's not good that day, but we can go somewhere next week (which is this week) smiling.
Today we were back from another tour, it was 10pm, I know we were both tired, but I knew her car wasn't at the airport, I asked her whether she'd like me to drop her off her home. She politely refused, saying she doesn't want to bother me, in response I said "I won't be bother, I want to be her driver tonight" she answered "aw I dontm want inconvenience for you, I'm in the opposite direction"
Normally she doesn't seem to be a shy girl. She seems like, if she wants something she would say it.
But again because of the fact that I'm her boss, it's very complicated. I can't read her reactions. I am known to be a pessimistic person in general. But in this case, I don't want to ask her for another date etc over and over because I don't want to create pressure on her, maybe she doesn't want it and is just being polite.
What do you think? Again, I'm not very familiar with the culture here. So your help will be appreciated.
Submitted: 1 year ago.
Category: Relationship
Expert:  TherapistJen replied 1 year ago.
Hi and welcome. I'm a Licensed Clinical Social Worker with more than 20 years experience working with individuals and families on a variety of issues.
Thanks for the info. Since these times spent together were at work, they sound more of a work nature than anything more. Her polite refusals to driver home, etc are indicative of that as well. Because you are her boss, I would be very careful of not crossing over the line where she feels uncomfortable in your presence or feel that she needs to attend these dinners because you are her boss.

It is probably a good idea to leave things as they are and go back to being her boss and not have dinners or other things alone that could be seen as dates. As her boss, it is your role to remain in a professional capacity.

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