Play The Field, Date On The Side

Dear Mason,

I met a guy and we started hanging out. On the second or third date, he made a comment like "let me know if you ever sleep with someone else." That combined with what I knew of him from our conversations, I figured he didn't really want to be committed (I was his first girlfriend), but I kind of put it in the back of my mind. We dated for 8 months and things were going well. Then, on our 8 month anniversary, we had a really serious conversation, with some of the things he said including "I feel like I'm leading you on. I can't say that I love you... I'm not sure I can love anyone at this point, or ever," (he had some emotional issues growing up) and "I really like hanging out with you, you're like my best friend, I feel closer to you than my own family, but I can't be committed to you at this point." He was unable to tell me if he thought his feelings would ever change.

For some reason I stayed with him, and now, 2 years later, things are basically the same. He's "been with" only one other person the whole time, but it's not for lack of trying. We get along so well though, and we really care about each other. Does it ever happen that when a guy gets more experience with other women, he eventually becomes "ready" to settle down? I mean, most people do end up settling down eventually, right? Basically, I can't decide if he really does just want more experiences with other women before he settles down with me (and even if that's the case, I don't want to wait around for 2 more years!), or if he just doesn't feel that I'm the right person for him to settle down with, but doesn't want to tell me that because he knows I won't be with him anymore after that. I do date other people, but things never work out, probably because I'm still so hung up on him.


- Very confused



Very Confused


Sounds like this guy has you on the back burner. There is never a set time when a guy is "ready" to settle down. A guy is ready when he meets the right girl. Family issues are always hard to deal with and make relationships a lot harder. I have been in that boat before but regardless of what issues my family has had and what that has done to me, in the past when I have met "that" girl then everything changed.

More experience with more women does not lead to settling down especially when you are part of his life when he is getting that experience. He is just learning that you will put up with it and that you'll keep waiting around. It sounds like he is stringing you along with false hopes of commitment so you are always close enough to be with but far away enough to not settle down with.

Right now he has all the dominance in your relationship because, like you said, you are still hung up on him and he knows that. He also knows that you won't date someone else when you are still hung up on him. The minute that you realize that you deserve more than what he is giving you is when you will gain the upper hand. Just because you have feelings for him, don't make excuses for him, that gives him too much power. Any relationship is not 50/50, its 100/100.

You need to give him the choice and stick to your guns. It's been 2 years now which is way too long. He knows if he wants to be with you. Any guy knows if they really want to be with a girl within anywhere from 2 weeks to 3 months depending on how much time is spent together.

Make him choose to be with you or not. You don't deserve to be strung along for another 2 years watching from the sidelines while he tries to play the field. You need to be ready to walk away if he doesn't want to settle down because if you don't then your dating life is history. You will be hung up on this guy for a very long time, all the while missing opportunities with guys who will sweep you off your feet. Guys like that are still out there, trust me, I'm friends with many of them.

Experience doesn't lead to settling down. The right person leads to settling down. Give him the the choice and if he can't see you as that person then it's a waste of your time and you need to move on.

-Mason Stanley