so i’m in a similar situation but on the opposite side of the glass.

I’m 30 years old live in Manhattan with my gf who i have been dating on and off since college for about 10 years now.
Following a break up of 9 months after another 2 years of dating, we decided to moved back in with each other on (11/27/14) with the intention this time to determine if we can build our lives together: get married and have a family.

Still after a couple months I’m not sure we’ve made progress and I can’t figure out if i want to marry her and be with her forever.

My eyes wander and I need advice. PLEASE HELP.

When I think about committing to her, I tend to focus more on our differences; what i’m giving up vs. what i’m gaining. People have said to me the grass is always greener on the otherside and I understand that yet it still doesn’t help me understand my feelings. A large part of me says you’re too young to “settle” even though I KNOW this is a GREAT GIRL and if i don’t propose to her in the next 6 months, I will loose her forever. There will be no more breakup/makeups after this (we’ve been through this too many times) and I fear i will be throwing someone really special away for the unknown because I am stupid/immature, etc.

I can see myself having fun going out in the city being selfish without it really interfering with my life goals… I say to myself, we’re living longer now, in five years I’ll be 35, more mature, wealthier, I don’t have a biological clock ticking…what’s the hurry? 35 for guys is still young and i’ll be older and there will still be many women… With this perspective then, maybe she ISN’T the right girl for me if i’m thinking this way. If i want to do these things and am not willing to give them up for her what does that say. Or maybe its just shortsided, immature and stupid like i said above.

What are the pro/cons of Settling down now/later. Giving up something great for the unknown – especially when you have something good though you’re unsure if you want to call it quits just now….

Another point with perhaps more susbtance is: without the “need to settle” maybe there is a more “right” girl for me in the future… with same religion/culture/socio-economic status…with less complications, more similarities, and perhaps allows for deeper connections. Its always been sad for me to think about not sharing holidays with her family (i’m a pretty spiritual jew) and its especially lonely when she doesn’t make these important religious things to me a priority. I question, Maybe I should just wait and find someone more like me to build a family around as I’m young and have time? She is making an effort to do an orthodox convertion yet i’m not sure how genuine that is. I question her level of committment and if that will endure through the years. With this being the #1 most important thing to me, i will be really dependent on her to transmit the traditions, which are not first nature, this to the children. Also, on a more superficial note i don’t really relate to her friends and family because they aren’t of the same culture and socio-economic background. It’s shallow yet its hard to find commonality and interest. Maybe I’m shallow but I need someone more like where i come from?

On the positive side, We’ve been together for 10 years now. She knows me best. SHE IS A GREAT GIRL – SAINT status. Beautiful. Caring, geniune, smart. a real catch. A big part of me feels a responsibility and loyalty to marry her because of how much effort and time she’s invested in me over the past 10 years. I’ve put her through so much and she has supported and stayed by me for all these times and the idea of not being with her or maybe never finding anyone as great as her is depressing. I don’t want her to feel like she waisted her time and crush her. She loves me so much despite the pain, selfishness, and anxiety i cause her. Though all the scars from the past I think have taken a toll on her and its hard to determine if that is only effecting our relationship now (with our state of ambiguity or if that will last later into the relationship). I question also if then maybe its better to just start FRESH with someone else now that i’ve grown/matured significantly in the past 10 years. Yet i’m not 100% sure how committed I am to our relationship and to her as a future partner and that’s not fair to her!

All her friends are married and despite being one of the best girls of the bunch – she’s the only one not married and i worry about her starting over after a ten year relationship . I care about her and I want to provide her with a great life. Is 30 an old maid in nyc? I wouldn’t want to do that to her.

So in summary. Its complex and I am confused. Evidently I am not ready to propose this minute and i’m trying to figure out if I should cut the rope and put this wondeful girl out of her misery & let her move on, or how do I get my act together, somehow get myself into a state of mind where I can propose and be excited about our future… and how do I do this?

Thank you so much for taking the time to read this… sorry its not better written.
Please let me know if you need more information so i can give you a better picture.

Thanks in advance for your help.