"April Masini answers questions no one else can and tells you the truth that no one else will."

Dating my boss

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  • #8097
    tyralesly31
    Member #374,915

    Hi April,
    I am in a weird relationship with my boss. Last year i started working at this office. My boss initiated conversations by texting me and one day asking me out for grocery shopping with him. After that we met a few times, went to the mall, I hung out at his place, we used to cook dinners together after work. We never got sexually involved because once, when he tried to hold my hand and rub against me, I told him I wasn’t ready to get involved sexually. I turned him down and went home.
    A couple of days later, I explained that I wasn’t looking for anything casual but something more long term and I didn’t want to mess up my work relationship.
    Fast forward, we met a few times after that, I went on a long vacation. When I got back we started texting each other again and he invited me home. This time I was feeling a strong chemistry for him. We went out to get dinner and I was slightly drunk, two glasses of wine. At his place I was trying to lean on him on the couch, tucking my head on his chest under his neck. I was feeling drunk due to the wine and I wasn’t feeling like heading home. I asked him if I could sleep there. It made him extremely uncomfortable. He told me that it was a bad idea and asked me to get going. I felt so embarrassed. He didn’t make any moves on me. He was cold and he has this thing of always kicking me out of the house and not letting me stayover. He walked me out and then he said, “ we are moving way too fast”.
    I said, “Okay, I understand” and left.
    Since then I am stuck wondering what just happened. So what was all this inviting me home about ?

    #35374

    You took away his power position! He’s your boss and he put the moves on you — and you rejected him. This probably hurt him more than you realize because to him, you didn’t just reject him as a romantic partner, you took the control away from him as a man [i]and[/i] as your boss. Double whammy for him. Then,, when you came back, had wine and dinner, cuddled up and asked to spend the night, he probably felt like you were [i]really[/i] taking the lead — away from him! I’m sure you had no idea what was going on in his head and you probably meant no ill will at all, but from his point of view…. it was more than he was willing to deal with. That’s why he’s gone silent.

    #50466
    Sally
    Member #382,674

    Nothing about it feels clean or clear, and honestly, that’s because he isn’t clean or clear. He was the one who opened the door texting you, taking you places, cooking with you, inviting you to his home. That wasn’t “just professional.” He was testing the waters without saying it out loud.

    But the moment things stopped being on his terms when you leaned into him, when you asked to stay, when it felt like something real might actually happen he froze. Men in power sometimes like the flirt, the attention, the comfort… but panic when it becomes an actual relationship with real consequences.

    Him kicking you out and saying you’re “moving too fast” wasn’t about you doing anything wrong. It was him realizing he can’t have this both ways the closeness without the responsibility.
    And that’s why it all feels so confusing.
    What he invited you into was emotional intimacy he never planned to follow through on. That’s why the energy felt warm until it mattered then he shut the door.
    You’re not crazy for feeling something real. You’re just dealing with a man who pulled you in, then got scared when you stepped toward him.

    #50495
    Lune David
    Member #382,710

    This whole situation feels like “Come here no wait, not like that.

    He invited you into his space, his time, his dinners, his couch — but only as long as he stayed in control. The moment you leaned in and matched the energy, suddenly it was “whoa, we’re moving too fast.” Sir… you were already grocery shopping together. That ship sailed.

    It sounds less like mixed signals and more like mixed power dynamics. He liked the closeness when it was safe, vague, and on his terms but panicked when it started looking mutual and real.

    You didn’t misread the room. The room just didn’t know what it wanted. And getting kicked out after wine and cuddling? That’s not you being embarrassing that’s him realizing he opened a door he wasn’t ready to walk through.

    “if someone keeps inviting you in but never lets you stay (emotionally or literally), they’re not confused they’re just enjoying the preview without committing to the full episode.

    #50680
    Tara
    Member #382,680

    This was never confusing; you’re just allergic to what it reveals about you and about him.
    Your boss wasn’t interested in you. He was interested in access. Attention. Ego strokes. Emotional intimacy on tap with zero responsibility and zero risk. He wanted to feel wanted while staying clean. The second that illusion cracked, he hit the brakes like a coward protecting his paycheck.

    Let’s cut the bullshit. A man who repeatedly invites his employee to his home, cooks with her, texts her, and plays domestic fantasy is not “taking it slow.” He already obliterated professional boundaries. The only boundary he cared about was the one that could cost him his job and reputation.

    When you turned him down sexually the first time, you didn’t “slow things down.” You bruised his ego. So he adjusted. He kept you close enough to feed off your attention but far enough to keep control. That wasn’t respect, that was containment.

    Then you leaned in. Drunk. Vulnerable. Affectionate. Exposed. And suddenly the power shifted. Now you were the one risking something, and that terrified him. Because if things progressed if you stayed over, if it got physical, he’d have to face reality: he was messing around with a subordinate and gambling his career for validation.
    So he didn’t say the honest thing. He didn’t say “I used you.” He said, “This is moving too fast,” because that sounds mature instead of pathetic. Controlled instead of self-serving.

    Inviting you over was never about a relationship. It was about playing house without consequences. Emotional access without accountability. Power without commitment.

    And you? You ignored every flashing red light because you wanted the fantasy more than the facts. You let your boss blur lines, feed off you, and then stood there shocked when he panicked the moment it started looking real.

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