Do I confess my feelings for him before I go?

Tagged as: Friends, Troubled relationships

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Question - (15 May 2013)

6 Answers - (Newest, 16 May 2013)

A female age 36-40, anonymous writes:

Over a year ago, I started working as a Team Leader in a customer service account that employed over 200 people. Since I was recruited externally, my lack of familiarity with the account and the people made me feel very apprehensive, but the manager who I directly reported to was so warm and friendly that in no time I got into the swing of things and settled in comfortably.

The manager and I would spend a lot of time working together, since he was in charge of training me. In the first few weeks it was apparent that we got along well with things aside form work, such as our taste in music. He would often say that he feels most comfortable with people of the same wavelength as his, and I felt that I was one of them. There were times when we would spend a couple of hours working together and our conversations would take a swift turn from work-related issues to music, film, books, and eventually even to family life, spirituality and relationships. He is known to be a very private person and is obviously very careful about things he says, but I could confide in him and sometimes feel he does the same. During my first few months, perhaps 70% of our conversations were about things unrelated to work, and I enjoyed them. I realized that I had become attracted to him, but was not sure if he felt the same way.

There was one time, when I was new, when we were discussing numbers and I raised a rather pointed but sensible question and he said, "You are so smart", and I didn't know whether he was being genuine or sarcastic. We had conversations on philosophy and what not, and on gender equality and other things where we end up debating, but in a good way. During my first party with the management team, he probably had a few too many drinks, and for a good part of the night he was teasing me, tickling me, and at one point he was standing so close (I could feel his breath on my face) to me trying to tickle me in front of everyone else, but I didn't want to think he was flirting since I think he does that to other female team leads who he gets along with. Not sure. He would also tickle me at work, when we're seated side by side and discussing reports, but they were always random moments and were not very frequent. When I was asked to co-host an event I--an event I didn't want to attend--he kept on cheering me on, screaming my name loudly and applauding every time I said something funny onstage. There was one time he asked me what I liked to eat, and which places I would usually go to. He would even initiate bets sometimes on random things and the condition would be whoever loses owns the winner lunch, but we never actually got to go out for lunch even when he lost twice. There are times when he'd make comments about how I look like, ("hey, it's the first time I've seen you wear a dress to work today" or "hey, you cut your hair")Then, at one point, we were talking about Christmas and how we choose to celebrate it, and he stopped mid-sentence and looked at me and said how baffled he was at the fact that we were so alike. When I created a presentation that the client loved, he would IM me at work just to say how much he loved it, and when I was being modest about it he continued to say how I did a lot better than he expected. And there were also a few times when we would suddenly IM about food and other things that weren't really related to work, but I couldn't determine if he was flirting or not. He would initiate all these IM conversations. He was probably only being nice too, right? From what I know, he doesn't do that to anyone else at work, but I could also be wrong, right?

During my birthday week, I gave him a copy of films and bands I love, and he texted me just to say how much he loved one of the bands and how he almost got to see them live the past year. He has never texted me before about things unrelated to work, and I doubt that he does that with other team leaders, so this was quite a surprise. We exchanged probably around two or three more text messages before I stopped replying, because I was getting really weirded out. This happened again, when he texted to ask if I knew about bars in the area where his band could play at. There was never any talk about personal feelings or whatnot, but the fact that we would be texting about things completely unrelated to work just caught me off guard. Again, he initiated all this.

There are times when he would get annoyed at me (work-related) and tell me straight, and then I'd stop talking to him, and then there were also times I'd feel a little jealous when he pays attention to other female team leads and then I'd stop talking to him and he'd always notice that. When I avoid him or stop talking to him, he would ask the people I'm close to at work what my issue was instead of approaching me directly. When things start getting slightly out of hand, he would call me into his office and we would resolve things but I would always chalk it all up to work and I could never tell him how I feel. There was this one time when, after he called me out on something, I didn't speak to him for a week and so he pulled me into his office and he apologized for calling me out and he said he was just stressed over stuff. He said I shouldn't be giving him the could shoulder. Then, for some unknown reason he asked me, "When you and your exes fought, do you always give them the cold shoulder?"

Then there was this one party we had where he walked up to me and we started talking, and I asked him to get me a drink, which he gladly did, and upon returning he was looking at my lips. My lips. I didn't know what that meant. I even thought I must have imagined it, but after talking to one of my friends at work, I was so sure he was staring at my mouth. One of the agents on the floor said he did that to her before, but it was so subtle and she didn't mind it at all since it wasn't like he was harrassing her or anything. (Note that this manager is the resident heartthrob, who happens to be effortlessly good-looking and charming, but he would never, NEVER in a million years make a move on anyone in the office because he just isn't like that. He found some of the girls at work cute and he would even tell me about them, but he was always clear about finding them pretty but nothing else. Besides, his work ethic is incredible and he is always so professional, despite being friendly and approachable and just so down-to-earth. Everyone adores him.)

Then a few months ago, we had a big fight because I argued with him in front of some agents and he said he felt I wasn't giving him the respect he deserved as my boss, and that caused a fallout between us two. He transferred me to another manager, and we didn't talk for 2 straight months, and within that time I decided to resign from work due to other reasons. I finally talked to him and apologized a few days ago. I still feel the same about him and my friends keep insisting that I confess my real feelings to him, since I am already resigning. But i don't want to since I have absolutely no idea how he feels about me and I fear the risk that I would take would mean the end of our friendship or, worse, a humilating experience for me.

I remember one time when I went to work feeling enormously depressed and I was crying in his office, confiding about home troubles and self-esteem issues (which I have a hard time getting rid of), and he said he thought I was a really, really cool girl. The other team leaders have been teasing me nonstop about my feelings in front of him, and I guess it's pretty obvious to everyone else that I care about him and I like him, but I just really want to know what I mean to him before I go. How do you think he feels, and should I confess?

View related questions: at work, christmas, depressed, flirt, jealous, move on, my boss, teasing, text

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A reader, anonymous, writes (16 May 2013):

This is verified as being by the original poster of the question

Thanks for all your insights on this. I get opinions from friends at work but sometimes fear their thoughts may not be as impartial and objective as I want.

I don't mean to sound so stupid but, I don't know if I would ever sum up enough courage to ask him out.I just really want to know how he feels without me having to, well, ask him out. I want him to do that and take the lead, if he ever feels the same :p