confusedcoworker Posted June 4, 2013 Posted June 4, 2013 Sorry ahead of time that this is long...but please let me know your thoughts! My boss is one of my best friends and has a son near my age. About a month ago, I had been out with her and she had invited her son to have drinks with us and his friend. We had fun that night, laughing and joking around and there were points that I questioned if he was flirting or just being friendly. Then, at the end of that night he told me to take his number because we had to go out without his mom and even told me about a few parties coming up that I should go to. Not sure if he was sincere or not, I took the number but, besides a few texts that went back and forth (usually initiated by me and never very flirtacious), I didn't want to be a nag if he wasn't interested and risk making the situation awkward since I am so close with his mother. This past Friday, while out with another friend, my boss mentioned that her son was downtown too and I might see him where I was. After his mom told me that, my friend told me to text him and find out where he was. He immediately texted back and said to come hang out with him. He met us at the bar we were at and I flirted with him most of the night, but he had clearly had quite a few drinks by the time he came to meet us. He flirted with other girls too (having broken up with his gf of a year about 2 months ago, his mom said he's been enjoying the single life lately...as have I). Every time he talked to a girl, he turned to me after and explained how he knew her...not that he owed me an explanation or that I ever asked for one. Still, he seemed to emphasize the fact that I was his mother's coworker, even somewhat jokingly introducing me as that to some of the girls. At the end of the night, I found out he didn't have a ride home and offered to give him one. In the car, he asked if i had been to the town beach and he said we were going to take that way home since I hadn't been. When we got there, he told me to park and we would go out on the pier. Once he got out of the car, he came to my side and held my hand for the entire time on the beach. We talked for a while and he kept saying how surreal it was and how glad he was that we went to the beach. Then, he became way more flirtacious. He said to me (out of the blue and completely off topic), "NOTHING will EVER EVER happen between us because you're my mom's coworker. Ever!" I shook my head in agreement and he added, "Even if you are cute." We ended up making out, although we agreed beforehand that we would never tell his mom. During our time together, he kept insisting he wasn't very drunk and had sobered up a lot since the bar. As we sat talking, he joked about one of his friends that had asked me out and said, "You don't want to hang out with him...you want to hang with me." Since then, I haven't wanted to bother him...not knowing what his intentions are. I invited him to go to a vineyard one afternoon, but he texted back right away and said he would but had to go to his best friend's bday. My question is does it sound like he is really interested in more or was it just a drunken hook up?? (honestly, I'd be ok with it either way) My other thing is, if you were interested in solely a hook up, you wouldn't choose me when there are so many other girls that aren't your mother's coworkers, right?!
drr6 Posted June 5, 2013 Posted June 5, 2013 Your boss thinks well enough of you to try to match you up with her son. He does not seem ready for anything too serious with you - because he just broke up, you are mom's co-worker, your astrological signs dont match, etc. "Take my number" + drunken hook-up = FWB potential. Not much effort on his part.
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