Flirty Or Friendly Boss?

[Burberryplaid]

I was promoted in February and started working for a guy who I knew for a couple of years. We were part of a peer training program and worked on a project together but were never really too friendly. Now that he's my direct supervisor we obviously have to talk daily and often. We have gotten to know each other on a more personal level. Some of our talks have been general "getting to know you" types (movies, sports, weekend activities) but we have also had interactions that some might consider to be "flirty" in nature. Examples:

 

1) A while back, his desk was moved to the other side of the floor and while he was showing me how to do something on Power Point he said "I know you miss me!" (We used to sit right next to each other)

 

2) He often sends me IM's to ask how my day is. It might not seem like a big deal but I know he does not interact with other employees who work for him this way

 

3) The day before a scheduled day off he sent me an IM that said "Can I change my mind about the day off? I need you!"

 

4) I jokingly act exceedingly confident with him & one time we were talking about nicknames (one of mine is Princess Cupcake) He replied back "I bet you never had conversations like this with your previous boss!"

 

5) He offers me his snacks (pretzels, m&ms)

 

6) He put on my sunglasses to make me laugh

 

7) He promised me cupcakes (although he has yet to deliver) because he

knows I love them

 

There are more things, but those are just a few examples. I know some it sounds like nothing but again, he doesn't act like this with all his employees.

 

I know we can't be together because I work for him, but I am curious as to whether or not he has feelings for me beyond friendship. (I am definitely crushing on him!) Does any of this sound like he is being friendly or does it sound like he is being flirty? I'd love to hear others thoughts.

Edited May 21, 2011 by Burberryplaid

[jackmark]

Well there's this guy at my school, he's pretty much my type (smart, funny, talented, tall, etc.) He's three years older than me though. And his younger sister is in my grade (she's not really a friend, but we have a decent relationship).

 

Anyways, one day around September-ish we were both outside waiting for a ride. It was quiet and I said "Man, this is awkward..." and then he says "No it's not. We are communicating telepathically" I smiled, and he smiled back.

 

Since we aren't in the same grade, we don't see each often. I see him in the halls only in the mornings, right before first period. When I pass by, he usually smiles. And any other time I see him, he smiles.

But the thing is...we don't talk.

 

There's something about his smile though...I don't know. It just ... ugh, I don't know how to explain. It's a mysterious and sincere smile. And it's been going on for weeks!