I’m 28 and I’ve been sleeping my boss who’s 54. We are hook up buddies. We both made it clear we didn’t want a relationship. We have been hooking up for six months. We have stuck to the rules until the last month or so. He’s been asking me to stay all night wanting to hang out at his house, and he’s been saying things like (This is the PG rated version. You can imagine what he’s really saying as he points to a certain part of my body.) “Who’s this belong too?” “You gonna share this with anyone else?” “I love this.” “I love sleeping with you.”
I’m not sure how to take any of these questions/comments. We went out to the bar together for the first time and he got there before me. When I arrived he informed me that the lady next to him asked him if he was there with anyone. I just looked at him and smiled and didn’t say anything. He then says “I told her my girl was on her way.” Again I just smiled and didn’t say anything. Once again I dont know how to take it. I’m confused about what should I do. Should I just let it go and see where it goes? Do I ask him where we stand? He wants to know who’s texting or calling me. He asks about my life. Does he want more than a hook up buddy relationship in your opinion?
The real question is, what do you want? You say you both made it clear you didn’t want a relationship but it sounds to us that you actually do in fact want a relationship with this man, otherwise you wouldn’t be wondering, or you wouldn’t care, what he’s thinking. Is that a fair statement?
You might want to read our e-report on Friends with Benefits/Hook Ups to see where we stand on these types of arrangements. But to sum it up. What we’ve learned over the years is that men enter into a hook-up arrangement because that’s exactly what they want. Women, on the other hand, enter a hook-up arrangement because that’s exactly what the man wants. Sure, some women feel as men do and are able to compartmentalize sex and love, but most women aren’t wired that way.
Okay, seminar over. You really want to know what he’s thinking? We’ll break it down for you.
First off, he’s sleeping with his employee, which is a huge no, no. We don’t know what business you’re in, but boss/employee relationships usually end at some point, and usually, not well. That’s definitely in the back of his mind, or at least, should be. Secondly, the two of you are in very different places in life. Does he have an ex-wife? Kids? Is he divorced? It’s very unlikely he sees you as something more than a beautiful trophy he can brag about to his friends, and to strangers in a bar. How do you see him? That doesn’t mean he doesn’t care about you, it just means he isn’t thinking long-term. Third, he loves having sex with you. He’s thinking he’s hit the proverbial lottery getting to sleep with a woman almost 30 years younger than him. He says all those provocative statements to you to keep you in the fold, a way to protect his “territory” so you won’t stray. Understand that he’s fully aware that he’s much older than you, and that you probably have other men interested in you. Even if he isn’t saying it, he feels insecure about the age difference.
Questions for you: What is your main motivation for being with him? Why a guy much older than you? What about a guy closer to your age? Someone you can build a life with? We’d love to know what you’re thinking.
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