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Is my older boss flirting with me?


Question Posted Thursday July 10 2014, 3:02 pm

I'm a 20 F and he's a 36 M. I'm cognizant of the age difference--my parents have the same one. I work in a drug store, not an office or anything, and I'll be leaving the job in several months.

Anyway, we've worked together for three years and I've liked him for almost the whole time. He was always rather distant with me but when I came back from school this past semester he started acting different.

He teases me constantly. He mocks my voice when I say something; ANYTHING and smirks at me when I whine about it. He puts price stickers on me, stands in my path so I'll push him out of the way, etc. We weren't very physical up until recently. Now we try to trip each other, he (gently) poked me in the kidney, and he did the same to my arm. If I stand on a piece of paper he's trying to get off the floor he'll bend down and grab my ankle to pull it up, and I grab him for balance.

He mimics weird tics I have, like pressing my nails together and rubbing my stomach. I kick at his feet when he does and he steps lightly on my toes.

I started texting him a few weeks back. Nothing pushy, just initiating conversation. He talked a bit at first but now he's starting to really open up and the past two days he started the conversation with me. We texted for six hours last night and made plans to go to the movies together.

We went to the movies last weekend with another coworker and it was good. Nothing happened, of course. But he offhandedly mentioned he wanted to see a movie and I said 'Movie date!' and he replied "you want to go??" I said sure and asked if we were inviting other people. He said we could but I said 'ehhh, they smell, though' and he agreed and said "well then, just you and me."

There have been other isolated incidents over the years. Last year before I left for school I was sitting in a room that bridges the store to his office. I was on the counter and he was passing through and I made a teasing comment that I was almost as tall as him. He's 6'1" and I'm 5'2". He stepped close to me, almost to my legs, and smiled, shook his head, stared right into my eyes, and said, "No, you aren't."

The only other major incident was also before I left for school. We were going into the office where another manager was and he was kicking at my feet or something. She threw the door open and said, "Why don't you two get it over with and date already!" I was sort of flustered because that's what I wanted so I only managed to mutter something about killing him if we were to date. And he didn't get uncomfortable like I figured he would. He laughed but didn't say anything.

So didn't know what to make of that... I don't know if he thinks of me as a friend or if he's actually interested in me.


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misspiggy answered Saturday July 12 2014, 12:48 am:
He is definitely flirting with you.

I do not know whether or not that is an indication of serious interest or just sexual tension and playfulness, though.

I suggest you start being a little serious with him once and awhile just to test the waters. For example, next time you go to the movies you could just say "Let's go to the movies". And if he asks about inviting other people say "No thanks. I'd rather it was just me and you".

Be a bit more open and maybe he will be too.

The world's prettiest pig,

Miss Piggy

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Dragonflymagic answered Friday July 11 2014, 11:17 am:
Thats some hard core flirting. Lots of it, the average type of flirting, but a lot of it just sounding like the kind of middle school pranks guys and gals pull on each other to show they are interested.

The only thing you did not mention is whether this guy has a girlfriend or a wife or whether he is single. You'll better know for sure if you are considering getting into a relationship with him.

At 36, he may just be a playful guy in nature...especially if he's like this with everybody. You'd know if this is how he is like in life. But to be honest, my first reaction to reading your descriptions to what he does is that I have never known an adult man to flirt that way. I was on dating sites for a couple of years and dated many guys and got lots of flirting but it was all at a different more mature level and nothing like what you describe which as I Said reminded me of middle school boys. It could be an indication that despite his age, what you have here is a man who has never grown up and is still much like a teen ager in his mentality which may explain why he feels more on equal ground by going after someone who is much younger. Not saying age gap is bad, just that you need to not assume that because he is older that he is more mature. You may never be able to expect the ability to be able to really count on him for all the things that matter in a long term relationship like marriage. He may not ever want the responsibilities of a mature relationship and prefers staying in the flirting stage...possibly reason he hasn't gone after you and started dating. I dont know if you know anything of his history, past relationships, whether at his age he has any kids or divorces. It is entirely possible too that he has already tried that route and found himself unwilling or incapable of being able to be the one strong adult half to a relationship. Go carefully if you decide to ask him out and start dating. If waiting for a him to ask, you may have to wait forever cus even though you respond to and join in the flirting, he doesnt know how you feel inside. Some people do take flirting on as a sport rather than as an indicator of interest in pursueing a relationship. Perhaps he thinks you are thinking of it as a sport or fun pastime rather than taking him seriously. I have no idea. The only way to discover anything with him would be for you to sit and engage him in a serious, indepth, adult conversation...if he is capable of that.
Good luck dear.

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Hardcore-Band-Geek answered Thursday July 10 2014, 7:36 pm:
That sounds a lot like a guy who has a crush. One time I wsa sitting at lunch (high school) and this guy (who i was starting to like at the time but wasn't sure) grab me from behind so i would squeak. I wasn't sure what to make of it, he's not a real touchy person. and then i found out we liked each other, he's my current boyfriend. It sounds like your boss likes you. I would go for it, just be careful :) have fun and good luck!

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