beentheredonethat34 Posted November 18, 2013 Posted November 18, 2013 (edited) Ok here goes: I really like my boss's boss (no direct reporting structure) and I think he likes me back based on the behavior below. He's retiring in April and is divorced. How can I get him to ask me out without being too forward? It's driving me crazy. 1. I recently emailed the maintenance dept for a new key card, and HE brought it to me (how on earth did he know???); 2. he always looks at me for longer than usual eg yesterday morning, I was doing filing when he came in through the backdoor which is separated from the filing area by glass doors. He stood there for a good 10-20 seconds just looking at me before going upstairs. 3. he is at the coffee shop (work cafeteria but located in another building) at the same time I am. I work odd hours so I find that unusual, and see it as his attempt to run into me 4. when I first started work, he always made reference to his 'ex' in my presence. I think he wanted me to know he was unattached. He also spoke a LOT about his daughter. I once brought my dog to work and he said he daughter would love my dog. 5. when I first started working here, there was a dying club called the 'movie club' where once a week a group of people would set up a laptop and watch a movie over lunch. By all accounts no one wanted to be in it anymore but he suddenly started attending, and when he didn't attend, he would come over while I was setting the equipment up and chat with me. I guess I should have been more receptive then but I didn't like him as much back then and also was very new so found it kind of weird that the boss would come into the movie room and sit down and talk with me when no one else was there. Of course that wouldn't be a problem now... 6. he ALWAYS compliments me - mostly my smile. He has said variously that it is 'infectious,' 'cute,' lights up the room etc etc. He also said I look like a flower. He always makes these compliments loudly in front of people which is doubly embarrassing, although of course, welcome. 6. last week my car broke down and I was walking to work. As I approached the building, he appeared from nowhere and practically RAN to get the door for me and asked me if I was alright. When I said I was just watched me till I was out of sight. I was sweaty and didn't want him to see me like that so I didn't chat with him as I walked away - I just wanted to disappear. 7. Lately I've noticed his new assistant always seems to be around and is extra nice to me. Not sure what that's about - maybe she's picked up on the above and thinks there's something going on. I just need him to say 'wanna go for coffee?' Edited November 18, 2013 by beentheredonethat34
Philosoraptor Posted November 18, 2013 Posted November 18, 2013 Well you should just say "wanna go for coffee?". Shyness will leave you alone and stuck with the "what ifs" forever, while just muttering those four words will at worst leave you where you are. At best they land you a date and a chance to really get to know the guy you're lusting over.
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