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I think I've developed a crush on my boss...

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Senpaiiiii~

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Uh, in Japan, your boss is not a senpai.
 
Don't shit where you eat...let her do the shitting if she's into that sort of thing. Also butt stuff. It's 2016 op, Kanye made butt stuff cool.
 
I don't understand the feeling of guilt. I've had a charming and hot boss before, and same with married business clients. You don't tell your instincts what to find attractive or not, so it isn't a moral/ethical issue. You enjoy being around them and that's all it is. There is no complication present if you don't let those feelings change your relationship. Chill out, man.
 
Are you able to have a working relationship with this person despite the fact that you are attracted to them? Once you can answer that and if you are, it would open up reasons to talk outside of work sometimes. I have been in work environments where this is fairly common. Depends on the type of work you do too, sometimes.
 
The thing most people seem to be glossing over is probably the thing that needs the most attention.

Those feelings about your gender identity won't go away, it's probably a good idea to seek out some therapy.
 
I'm in a similar situation except it's not a boss but a coworker whose new. The good thing for me is that it's a temp job so I think it'll work. But don't feel bad about being attracted to your boss, it happens. I've had hot bosses too and the best thing you can do is just go with the flow. Fighting too much one way or the other tends to make things really awkward.
 
IDK, OP, it sounds like you have some stuff of your own to sort out before you can act with a clear head. If you question your gender identity and have depression, maybe you should put her on the back burner - at least for now. Just be amiable with her in the mean time. Tread carefully and don't rush things right now would be my advice.
 
Raise your pen0r for her, and then she'll raise your paycheck for you!!!

J/K OP, don't do it. Much regret you shall have (I know from experience -_-).
 
Just take it out and see how the boss reacts. If the grip is strong, you're good to go.

Being serious: Dont' ever (ever) listen to the whole don't date co-workers. That's just baloney.
 
Just go for it
In the end most relationships don't last in any firm.

I mean most people we know now won't be in our lives in 5 years. Won't matter mostly.

As long as you don't scare her or piss her off while over you

Ask her out to dinner
 
She could lose her job since she is your manager, so there's nothing that could happen there that would go well. Would be different if she was just your coworker.
 
don't listen to all the betas in this topic op, they've probably just been turned down by bosses in the past or never had the balls to go for it and watched from afar as their boss/coworker found someone better. listen to your gut and at least slightly go for it, you never know until you try. who cares if you work together

Just go for it
In the end most relationships don't last in any firm.

I mean most people we know now won't be in our lives in 5 years. Won't matter mostly.

As long as you don't scare her or piss her off while over you

Ask her out to dinner

.
 
I've been meaning to make a similar thread for days now. Difference being that I'm gay and my boss is straight, married, and has kids. I was attracted to him the moment I met him, but as the months have gone by the attraction has moved beyond purely physical. In fact, it isn't really just a crush anymore. I'm pretty sure I'm in love, even though I know nothing is going to (or even could) happen. He's such a good person, has always been kind to me, and we get along well, which has only exacerbated the situation. I'm trying to just enjoy the ride while it lasts, but at the same time I'm paranoid about how obvious my feelings for him must be and don't want to make him uncomfortable.

Unrequited love is always rough. Unrequited love for someone you have to spend 8 hours a day with, are sexually incompatible with, and who can never even find out how you feel about them at risk of jeopardising your career and the pretty awesome working relationship you have with them, while also battling mental issues that compel you to overthink stuff...yeah, "rough" doesn't quite cover it.
 
lately I've begun to have old feelings of wanting to be a woman, which is something I've struggled with for years and somewhat suppressed it for awhile, but recent events (such as how it's become more accepted to have such thoughts) have had those thoughts bubble to the surface. And I guess all this has sort of come together and made me extremely stressful, in addition to my recent D.U.I. restricting my social life to the point work is my main source of interaction.
I feel this, and your lack of close friends are more important matters. It seems she's your source of comfort in a pretty isolated life, in which case, it'd be silly of you to act upon your feelings. It's better for you to resolve these issues first before you potentially further burden yourself. Regardless of any of that, don't feel guilty about your attraction to her. That's normal, and it's not something anyone can control.

Sidenote, an employee of mine once came on to me aggressively, and lost her job because of it. Whatever you do end up doing, at the very least, don't go that route. It'll look a hell of a lot worse since you're a man (or I should say that's how you appear to others since you seem confused about your own identity at the moment). Double standard it may be, but that's reality.
 
Did anyone read the whole OP or just assumed things from the title?

Because reading this:
honestly it's not even really a "I want to date" thing, more of a "I really like working for this person and would be interested in connecting outside of work", since right now I don't really have any close friends.

Tells me you're not really crushing, but are more enamoured with the exciting possibility of forming an intimate friendship with someone. Think of it as "your new best friend" kind of thing. I get excited that way whenever I met someone who I believe could form a part of my select group of very close friends.

Just my two cents.
 
It's kind of a bit odder of a situation too because from what I've heard she's into women, and lately I've begun to have old feelings of wanting to be a woman, which is something I've struggled with for years and somewhat suppressed it for awhile, but recent events (such as how it's become more accepted to have such thoughts) have had those thoughts bubble to the surface. And I guess all this has sort of come together and made me extremely stressful, in addition to my recent D.U.I. restricting my social life to the point work is my main source of interaction.
DUI aside, that's an interesting revelation.

"She's my boss"

"I heard she's into women"

"I could be a woman"

Shut this down now.
Why? It's just starting up.
 
Don't shit where you eat. Don't even think about shitting where you eat.

I've had frequent sex with five different coworkers. Had a serious relationship with one of them.

No regrets. If she's not a psycho, can keep things in perspective, and gives you the go ahead then have fun, OP.
 
Well, I took your guy's advice (to not worry about things) and today felt a lot better about the whole situation, the biggest issue though is I get nervous talking to her so now I'm worried my boss thinks I'm a total wimp.

Though she did asl me to come in and do one of the important late shift jobs which is nice, the best thing is that she's finally letting me try out other departments in the store when previous manages always blew me off when I expressed interest. Well I don't know what she thinks of me otherwise, but at the very least she seems to think I'm a competent worker which is pretty nice since I think sometimes people confuse my nervousness and more feminine personality for me being incompetent.

Well, hopefully overtime things chill down. I think it's just the holidays getting to me and everything due to the expectation right now to be with someone.
 
One of my boys at work has banged out like 50 women in the company, some were his superiors. Dude is insane.

Are there any signs from her? If not, bail out.
 
I think a minority of people read the actual first post.

Your gender issues and depression should be a first priority, do you think if you got with your boss she would be able to emotionally/physically support you through a gender reassignment? I'm not saying she wouldn't but it would be a test of any relationship, especially a new one.

Focus on what you want to do first dude.
 
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