I’m pretty sure one of my bosses has feelings for me

I’ve had a gut feeling about it for a while. But for many reasons, it would be risky for him to be more forward about his attraction. For one, I’m currently in a relationship. I’m not happy in this relationship, though and I plan on breaking it off soon. It’s actually a subject my boss and I have talked about before and he’s asked me since if I’ve gone through with the break up yet. On top of that, the person I’m currently seeing is a female. For a while I’ve thought I was a lesbian, but I definitely have feelings for my male boss. So he thinks I’m totally not interested in him. And he’s my boss, so a relationship between us would be inappropriate.

I’m hoping once I break up with my girlfriend I’ll get a more clear signal from him, but I’m worried he won’t ever realize I like him too. And I don’t want to come on too strong in case he’s totally against dating someone he works with. I personally think we could make it work, but it’s a messy thing to do.

Once I’m single, how can I let him know I’m interested without making a fool of myself? I feel like since he thinks I’m a lesbian it’s going to take a really obvious signal to let him know. Would it be too forward if I casually mentioned something about possibly being bisexual or saying that I want to try men out for a change?

Help me understand... you believe that dating your boss would be messy (it absolutely would be)... and that a relationship would be inappropriate... so why do you want to move forward with this?

You are setting yourself up for heartbreak and possibly losing your job if it doesn’t work out.

And if he isn’t interested, you are setting yourself up to make this an uber awkward situation at your workplace.

Not to mention you are still in a relationship.

If anything is messy and inappropriate right now it’s your thoughts and actions about this situation.

Consider getting yourself sorted out before you make a move on anyone, nevermind your boss.

Dating your boss is always a bad idea. Keep in mind that if you break up with your boss, you're probably out of a job. But if you want to go ahead, I don't think you need to have a "talk" with him. He'll probably make a move on his own once he finds out you're free. Or you simply could say, I'm feeling, sad, how about taking me out to cheer me up? If he's single himself, he'll probably get the message.

This is messy.

Break up and be single for a long while. Don't think about this. You need enough space for a good while to consider everything and have a clear head when you decide if your job is worth this possible relationship.

It would be best to stop string your gf along. Also talking behind her back to your boss lacks courage. It's unfortunate you have a crush on the boss, that would be a mess and he would be a fool to go there.

Why not explore your sexuality, etc without stringing your partner along and without coming on to your boss..

I’m currently in a relationship. I’m not happy in this relationship, though and I plan on breaking it off soon. It’s actually a subject my boss and I have talked about. I’ve thought I was a lesbian, but I definitely have feelings for my male boss.