Dear Dan: I’m a recently divorced single mom and full-time student. I’m really beginning to hurt financially and have decided to start working as an escort. I am at a point of great emotional stability, happiness, and confidence — all reasons that led to my decision — and I’m surrounded by people who love me and won’t judge me. (Not that I will be telling most of them.) I’ve been seeing a man who I like, but I’ve made it clear that I am not committed to him and can see him only once a week. I’ve explained that I don’t think I can ever be monogamous and I do not want a relationship. He has struggled with this and told me early on he was in love with me. We have amazing sex, and I think this causes him to have a hard time understanding why I don’t want a relationship. I do not want to tell him I am escorting. I feel the fewer people who know, the better. And I don’t know him that well, as I have been “seeing” him for only six months. I know he would want to know, and a huge part of me feels that the right thing to do is be honest with him if I am going to continue seeing him. I also know that cutting him loose would hurt and confuse him, especially without being able to give him a reason. How do I handle this? What is the right thing to do? My site goes live in three days, and what’s keeping me up at night is not how best to verify clients, it’s what to do about the man in my life who I respect and love, even if I am not in love with him.
—New To Escorting
Dear NTE: Let’s set the escorting issue aside for a moment. You don’t want the same things (he wants monogamy and a defined relationship, you don’t want any of that shit), you don’t feel for him the way he feels for you (he’s in love, you’re not), and you’re a busy single mom and full-time student — all perfectly valid reasons to end a relationship, NTE. You aren’t obligated to tell him that something you were thinking about doing but haven’t yet done, i.e., escorting, factored into your decision to cut him loose.
While I definitely think people have a right to know if their partners are escorts, I don’t think people have an absolute right to know if their partners were escorts. So if the sex is really good, and you think there’s a chance you could one day feel as strongly for him as he does for you, and you’re planning to escort only until you get your degree, NTE, you could tell him you want to take a break. Explain to him that you don’t have the bandwidth for a boyfriend just now — kid, school, work — but you’re open to dating him after you’re out of school if he’s still single and still interested.
Dear Dan: I’m a 30-year-old single monogamist, and I recently realized I’m bisexual. I feel much happier. Except I recently crossed a line with a very close friend of mine, a man I’ll admit to having some romantic feelings for. After he broke up with his ex, I started getting random late-night text messages from him. And a couple weeks ago, we hooked up sans penetration. We acknowledged that we both have feelings but neither of us is in a good place. He’s still dealing with the end of his LTR, and I am only just coming out as bisexual. I love this person and our friendship is important to me, but I can’t stop thinking of the possibility of us being together. I’m confused by the timing and I wonder if this is real or just something I’ve allowed to distract me — or both! Also, what would this mean for my bisexuality? I’ve been to this rodeo before — meaning opposite-sex relationships — but what about the part of me I haven’t fully explored?
—Between Every Thorn Solitude Yearns
Dear BETSY: You describe yourself as a monogamist — so, yeah, entering into a committed relationship with this man would prevent you from exploring your bisexuality. And the timing feels off: He may be on the rebound, and you’re still coming to terms with your bisexuality. So don’t enter into a committed relationship with him, BETSY, at least not yet. Date him casually and keep hooking up with him, with the understanding — with the explicit and fully verbalized and mutually consented to understanding — that you will be “exploring” your bisexuality, i.e. you’ll be getting out there and eating some pussy.
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