I (24M) currently work as a banking trainee, and I have three days left at the branch. One of my coworkers (34F) has shown repeated signs of interest. We’re both in retail banking now, but when I first joined, I was in securities. Despite being in a different department, she would regularly come to my desk to talk, touch my arm or shoulders, and once even gave me a shoulder massage out of nowhere. She would ask personal questions and seek eye contact constantly. When I looked at her, she’d always smile.
She once showed me a picture of herself and asked what I thought. When I said her jacket looked childish, she teased me with: “You’d probably tell your girlfriend what to wear, right?” and tested my confidence with follow-up comments.
Eventually, she asked for my number and said: “We should get a coffee sometime.” So we met up for the first time outside of work. Right at the start, she told me that her boyfriend had dropped her off and was out shopping during our meetup. That caught me off guard, but I played it cool. She already mentioned her boyfriend before she started flirting with me at work
The date itself was nice but unclear. I told her she looks great when we met, and she returned it. I asked how she had perceived me when I first joined the branch, and she gave a personality-type answer (Persolog “blue” – analytical, structured). I told her my impression of her, ending with: “…and then I wondered: is she flirting with me?” She laughed and said something like, “I’m just a very nice person.”
Later during the date, she casually said: “You could come to my place sometime… maybe bring someone with you.” Which was weird – like she wanted to invite me, but also protect herself from the implications. We ended the date with a warm hug, and she said: “We’ll text.”
She also told me she trusted me more than other colleagues and opened up about past mental health struggles and issues at work. Ironically, she told me that another male colleague (married with kids) had tried to hit on her, and she judged him harshly. That struck me as hypocritical, since she was meeting me behind her boyfriend’s back.
How do I approach this situation if I want to sleep with her – but also leave room for something more?
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