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, we got back together and after another 2 years of dating, we decided to moved back in with each other on (11/27/14) with the intention to determine (finally) 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 now 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 something special away for the unknown perhaps because I am too stupid, immature, and selfish to appreciate who great she is.

A large part of me wants and sees myself enjoying having fun/going out in the city being selfish without it really interfering with my life goals… I remind myself we’re living longer now, in five years I’ll be 35; more mature, wealthier, better looking? I don’t have a biological clock…what’s the hurry? 35 for guys is still young and i’ll be older and there will still be many women/options… perhaps i’ll even know myself better then. 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 about me or our relationship? Again, maybe its just shortsided, immature and stupid like i said above. A fear I have is wanting to play and then when I am ready i’ve passed up so many good girls that I just can’t find a good connection with anyone and then I settle THEN for something less! oy VEY!

Can any guys comment on what are the pro/cons of Settling down now vs later? Giving up something great for the unknown?

Another point with perhaps more substance 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 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? While She is making an effort to do an orthodox conversion (no small commitment) a part of me questions her motivations and how genuine that is. I question if her committment to judiasim 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, 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 augments the religious differences as well. Yes It’s shallow yet its hard to find commonality and interest. Maybe 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 PHENOMENAL GIRL – SAINT status. Beautiful. Caring, genuine, smart. a real catch. MAYBE I’M JUST A GREEDY SELFISH IDIOT.

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 from all of the emotional scars from the past, due to unpredictability, not having a “partner”, etc etc. I think it may have taken a toll on her and its hard to determine if this is only effecting our relationship now (because of 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. Maybe i’m just not a good partner and i need to tell her this because she deserves better…

Probably least important is that All her friends are married and despite being the best girl of the bunch – she’s the only one not married because of me, 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 but maybe i’m not the right guy!? Is 30 an old maid in nyc? Did I make her an old maid? I wouldn’t want to do that to her…

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 wonderful girl out of her misery or how/do I get my act together, screw my head on straight, man up, become confident with my decision, and get myself into a state of mind where I can propose and be excited about our future…

What do you think?
Thanks in advance for your help.