Is he just a boss.. definitly a friend... or more?

I've been working side by side with someone... a little older... like 40 and im 27... for a year now and weve gotten to know each other quite well. We began going out for drinks with co workers and then just the two of us. When i broke up with my boyfriend he seemed excited and began to stand a little closer ( im one who likes my perso al space and he was in it) and he said if i ever wanted to catch a movie or something just ask. We began hanging out outside of work by ourselves and he always paid. Things have gotten slightly flirty but nothing physical. We smile every time we see eachother ( even when we have to be at work wayyy early), i can feel a difference in our relationship after the break up, and a couple people at work have commented. He once asked me to dinner at a place his friend owned and it seemed like a date but the day came and he never brought it up at work and it never happened. He insisted on taking me out on my birthday and paying for it. Also he got tickets to a concert and pulled all kinds of strings for both of us to have the day off to go. He is going through a divorce (started before we met) and im not one of those girls who has no self esteem but im not a model and he's not a 10 but a catch at the same time he knows im not the kind of girl whos a hookup. I have never had a connection with anyone quite like this. I can't figure it out. I could see us having many of different relationships; all of which last a while because i feel he will be in my life for a while. I just can't figure out which one either mentor (him) mentee (me), friends or more. HELP!!!


Most Helpful Guy

  • Sounds like he genuinely has feelings for you. When a guy is trying his best to do things with you, paying for everything, asking you out to do things with him every chance he gets, getting closer to you, flirting more with you, wanting to be around you more, it's a clear sign he wants to be with you. This is definitely more than just friends for him or he wants it to be. It's the same for guys as it is for girls. Take it from your perspective. If you were really wanting to be with someone, wouldn't you try your best to spend time with them no matter the cost? Same thing here. The divorce, yeah it can be complicated, but unless there are kids involved, then to me it sounds like he doesn't feel much of a connection with his ex anymore and the divorce is more of a legal formality. Kids can be complicated, but as long as he doesn't expect you to be a mom to them, then it's not really an issue either

    It's really hard for anyone, guys as well, to start wanting to be with someone after they get out of a relationship such as a divorce. Not that he has feelings for her, but it's more of a you don't know what to do anymore when it comes to meeting someone again or dating again. You just don't. You didn't live like that for a long time, so you don't know what to do anymore and you're not in that frame of mind anymore. But, if he is trying his best to be with you, chances are, he really wants to be with you and is in the frame of mind to be with someone new. So maybe try asking him out on a date or talking to him about your relationship and how you feel about him.


Most Helpful Girl

  • What you are is looking for a new job. Unless you marry him you've already made this into an uncomfortable work environment if there is a rift. I do not think bosses and wmployees should be beyond casual friends. It is an uncomfortable dynamic.

    If you feel like there could be more, perhaps consider looking into a transfer. A new job is a small price to pay for true love.

    So be forewarned however, divorce is morw complicated and painful then a breakup from a lover. Sorry. Its just truth. And know its not final until a judge rules its final. This means there ia a chance, even if he says he would never go back, that he might go back, even after dating you, for many reasons. And sometimes it hurts more when a man leaves you for his soon to be ex wife, especially when you know he doesn't love her...


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What Guys Said 6

  • Not a 'Mentor' just a 'cradle robber'!!
    True Mentors NEVER cross the line and become personal, like you describe!
    Mentors are there to encourage you, to teach you, and make you a better person, not just try to get in your pants.

  • You're in a gray area. But note that 1) he's in a rebound frame of mind; 2) there's a reason he and his wife broke up..3) There's already gossip at work about you,
    4) there's a significant age difference, and a large relationship experience difference (he's been married, you're apparently single and unattached)
    5) You're forced to get to know each other in a work situation.

    Think of what happens if you get together and then break up...

  • It seems like it can go somewhere but since you're both fresh from breaking up from someone may be why it's going slowly but that could be a good thing too , just take it slowly and get to know each other better, the age gap is not bad since you're much older now

  • who's the guy you're status says you're crushing on?

    • The one im asking about

    • Show All
    • I appreciate your opinion. The age is a factor, I've always gone for older guys. I know how that seems to people. I just want a man and all the guys i seem to meet my age are imature and not on the same page i am

    • love comes to you when you least expect it, that's all i know. take it or leave it

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