Hi Jenny, I met a woman on a dating app who I find very interesting. We texted for a while, and finally met in person recently. It went okay, but there were a few awkward moments. She indicated that she was looking for something more casual, which isn’t my usual MO but I am down for. We still text occasionally, but not nearly as much as we did before meeting. I really don’t want to run into a dead end. Should I express my intentions in continuing to get to know her, or just ask to hookup? Thanks, Confused Dear Confused, I hate to answer a question with a question — but what do you really want? If you think hooking up would be fun and wouldn’t leave you disappointed, then go for it. But if what you really want is to get to know her in hopes of something more than a hook-up, then you have to tell her. And you have to be prepared to be rejected. Here’s the thing, although it may be hard to see, it’s better to be rejected now for what you do want rather than accepted for what you don’t really want. Play out the scenarios in your head and see how they sit with you. How do you imagine feeling after hooking up knowing that’s all there is? Unless you feel giddy about that, why bother? Casual sex is only fun if it doesn’t leave you empty and wishing there had been more to it. How do you imagine feeling after telling her that you are open to taking it slow, but you are looking for more than a one night stand or a friends with benefits situation? Even though you may be rejected and that rejection might sting, it may be a lot less painful than having her and losing her all in one fell swoop. And, who knows, you may end up surprised on that off chance that she is willing to take a chance on you despite her own fears and insecurities. That’s unlikely, sure. But you have to tell her the truth, your truth, whatever that may be. As women, we are trained to accept scraps. But we deserve it all. It is far better to wait for what you really want. Trust me. It will come. You want a relationship, but all she’s offering is a hook-up. Don’t settle for scraps. You are worth so much more than that. Best, Jenny Send your question for Jenny to [email protected]
