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His demeanor is flirtatious, I def don't get the friend vibe, but he doesn't seem to be taking me seriously in a dating situation either... Whats the deal??

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Question - (17 January 2011) 1 Answers - (Newest, 18 January 2011)
A age 36-40, anonymous writes:

So I'm 25 and he's 28, we work in the same office. From the night of the first happy hour he and I have chatted each other up. The next day he started with the daily emails on the company email, which continue to this day. Right away he asked me to lunch, but was weird about paying. He seemed just a tad surprised when I let him pay, so I covered by saying that I'd get the next one. He agreed pretty easily to that. So I did, the next time he asked me to lunch, I paid and he let me. He has been very consistent for a few months now with coming up to my desk twice a day to talk. It took him a while to ask for my number, but he's had it for quite some time now. He called me twice one night early on and I blew him off, so he's been sticking mostly to texts. He does that consistently. He asked me out for drinks one night, he paid for a white wine and whatever he got... See, I'm used to being taken out, so I guess when a guy asks me out I just sit down and expect him to go order and pay. We've had a few sporadic lunch dates here and there, sometimes he pays (esp in front of his friends,) sometimes he lets me pay for my own. He asked me out for a weekend night, and I canceled last minute, so we did a day date...he expected to pay. A few nights ago he asked me THE DAY OF a movie premier if I wanted to go, his friend came by tickets...so we went (we work in NYC,) uptown after work, met his childhood friend who brought his own casual date, and saw a movie. The guys suggested drinks afterwards, I declined and went home. So that's where we are: he still stops by my desk routinely. He gets off work at 5, I get off at 5:30. It's very common for him to linger at least 15 minutes after 5, and twice he even stayed all the way til 5:30 just to walk out with me, but then didn't try to hang out just said our goodbyes on the sidewalk and headed for separate subways. It's bizarre but he almost WANTS his friends and co-workers to see us together...the sinister part of me suspects perhaps he wants to start rumors that aren't even true....but most guys live by the phrase "don't sh!t where you eat," so it's soo weird that he almost wants to become a topic of gossip, but he hasnt made any real strides to see me much outside of work consistently...once he invited me to lunch with his other friends from the office, but it's usually one-on-one, although we often run into the other guys on the street. If he doesn't have lunch with me, he's with them..and we often see them when we're out together. Clearly his demeanor is flirtatious, I def don't get the friend vibe, but he doesn't seem to be taking me seriously in a dating situation either... although his friends all have this understanding that there's something going on. Forgive my rambling, but I'm confused. and if it were 1 month in or even 2 months in I would be cool about it but here we are spinning our wheels going on 3 months and ....???

Oh, he's been with the company for 3 years. I started 3 months ago... as far as I know, from ppl who've worked with him, he hasn't had an inter-office relationship before (not that he hasn't been known to wink at a girl or two, but nothing serious.)

View related questions: co-worker, flirt, text

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A reader, anonymous, writes (18 January 2011):

Perhpas you should stop looking at him through a telescope.

You are trying to figure him out, but even if you knew how he felt exactly, I doubt from the sound of your post, you would know what to do about it.

But since you want an objective opinion about him, here it is: It sounds like he is interested, but it sounds like he's shy and waiting for you to show definitive interest in him.

You are reading a lot into details. You obviously keep track of how and when he pays for your meals, how early in advance he asks you on a date, who he is around when he talks do you.

Perhaps you should ask yourself if you like him and enjoy his company? If you are interested and want to do more than "spinning your wheels" with him, why not show some genuine interest instead of blowing him off?

If you don't care about him, but you just like watching him like a national geographic special, it would be a lot kinder and humane to tell him bluntly that you aren't interested.

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