I'm sort of seeing this guy I have dated on and off for years. We always seem to end up together any time we are single. Part of me feels like maybe I should just stay with him, since we keep ending up back together. But then also I sort of feel like he is using me, in that "whenever he is lonely, he thinks, she'll always be there" kind of way. You know? I don't know what to do or how to go on like this. I'm totally confused.
Should I or Shouldn't I?
Dear Should or Shouldn't,
Obviously you two have an authentic connection. You don't keep going back for more dessert cause it's pretty. There seems to be some substance here. You clearly like him, and he apparently likes you. So what is holding you both back from giving it a real go?
But let's forget about him for a moment. How do you feel? What do you want? What do you like about him? Try writing a "stay" and "not stay" list. Sometimes putting pen to page invites hidden truths to emerge.
That list might help you figure out why you keep breaking up, too. Is it that he just gets on your nerves after a while? Or that you are afraid of commitment? Singletons tend to create another sort of list, about Mr. or Ms. Perfect. The requirements might be utterly insane, the fantasies too fantastical to achieve. And then no one is good enough. Can you move past the way he leaves toothpaste all over the sink, or his annoying friends, or are you stacking up the faults so you can reject even trying the "real thing" with this guy?
And have you ever talked to him about his feelings? Have you two ever even addressed the fact that you keep seeking each other out, time after time?
It's time to talk. Being up front with him gives him the opportunity to be up front with you. Ask him whether he is also aware of your pattern, and if he knows why he keeps coming back to you. Is he using you as a convenient partner in between other relationships because he doesn't want to be alone? Is he hanging around for sex? If that's what you want, too, then you might just agree this is a nice little arrangement. No attachments, no expectations and a strong physical connection can be very rewarding and liberating.
But if either or both of you secretly wants to explore something deeper with each other, well, that conversation is going to go to a place that I cannot predict. The important thing is to be honest and real and respectful with each other. Honor the relationship and attraction you've had so far, and just see where it goes from there. You might both be very surprised.