Can I Turn My Boy Toy Into a Boyfriend?

Ask Demetria: Changing a friend with benefits into a real partner can be trickier than you think.

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I have a male friend with benefits/a jump off that I actually like beyond the sex. I admire this man's hustle, work ethic, goals, etc. How do I go about pursuing a more serious relationship with him? I have read your book and understand what may or may not result from this, but the answer is always no until you ask. Just curious to know where I should start and what I should say if I decide to pursue something more with him. --R.G.

I'm an advocate of a single woman getting hers, sans a relationship. Women have desires, too, and as far as casual sex and health go, it's far better to have one partner fulfilling your wants and needs than several. That said, if you're grown enough to play adult games, you also need to be ready to play by the rules of them. 

Since you've read A Belle in Brooklyn: The Go-to Girl for Advice on Living Your Best Single Life, you know I talk about the rules for casual sex in "A Good Jump Off Is Hard to Find." Rule No. 6 is "JO's don't grow into more. So if you want more than sex up front, don't think sex is the way to get to that 'more' point."

Of course, that's a generalization. Everyone has a story about some friend's cousin's best friend who started off as a jump off and is now married to that former sex buddy and they're raising two kids in the suburbs. It happens. But it's the exception to the rule. The problem is that everyone sees their situation as the exception, when really, it's the rule.

Allow me to explain the logic. Say you have a friend who gets a job managing a new club, the hottest spot in your town. It's a classy place where entry is only at the doorman's discretion. You arrive, text your friend that you're outside, and he comes out to get you, skipping you past the long line of paying patrons.

You're escorted to VIP and you can swill rosé like Rick Ross, anytime you desire. This goes on for months, but then one day you show up expecting the poppin' bottles all-access you've become accustomed to. You text your friend to say you're outside and he tells you, "Sorry, $20 at the door."

You aren't going to wait, much less pay. Doesn't matter how "swexy" the spot is. You will drive to another venue, wait to get inside, buy overpriced drinks at the bar and complain to the bartender about the nerve of that first place that really isn't all that, anyway.

This isn't much different from the (sexist) old adage, "Why buy the milk when the cow gives it away for free?" In the old days, that was the logic for not having sex before marriage. But viewpoints on sex have evolved (or devolved, depending on whom you ask). Your friend with benefits has no logical reason to commit to you when you've allowed him all access to a valued benefit of a relationship without requiring any sort of effort of commitment up front. If he's going to enter a relationship, it will more than likely be with someone whose value, in his eyes, is an entry fee worth paying.

To ask about a relationship at this point is setting yourself up for a great likelihood of rejection, perhaps the most-often-expressed fear of my lady clients. But to hear "no" (or its equivalent) won't kill you, even if the sting of pride in your chest might make you feel that way. And you might just be that one-in-a-million lucky exception. Who knows?

The next time you're alone with your FWB, and after you have sex -- the time just after an orgasm is one of the most honest times in a man's life -- tell him what's on your mind. A casual, "So I've been thinking ... " is as great an intro as any, and from there just tell him plain that you want to be in a relationship. End whatever you say by asking him pointedly, "What do you think about that?" Then wait and see what he says.