The Guy from the Wrong Side of the Tracks

A woman seeks advice about whether or not she should continue dating a man who is so different from her.


The Boy from the Wrong Side of the Tracks

Dear ASK REAL GUYS: I will start out with a bit of background. I was married at 25, divorced at 31 – because my ex husband betrayed me in some very fundamental ways – I won’t get into that. I come from a fairly conservative and successful Indian family; I have a Master’s Degree, a close to six-figure salary, and am very independent.

I started dating again and have been exclusive with a guy since last October – so a little over a year now. He is seven years younger and pursued me for about six months (we met at a local bar and became friends) before I agreed to go out with him.

The reasons I hesitated? His age (younger), education (high-school grad and certified mechanic), lifestyle (even though he grew up in a wealthy suburban Philadelphia neighborhood he turned to the streets early, small-time drug user and dealer, did three months in jail for a DUI at 20). He doesn’t have a steady job – says he can’t get auto jobs because of his record – but works in catering with a couple partners who are trying to start their own business.

He quit drugs (dealing and using) and alcohol completely before we went out because, in the six months we were friends, he said he wanted to be ‘respectable’ for me. He said that I gave him a reason to want to be better, whether I was with him or not.

The reasons I have been with him for a year now? He is kind, compassionate and sensitive to my every need. He cooks for me, cleans my house, takes care of my cat, gives me the best sex I’ve ever had and is basically like a wife. And every successful woman in a demanding job wants a wife, right?

When he has money, he pays for food and household things. He says he wants to marry me, and has asked me at random times over the past year. I don’t want to have biological children and he is willing to adopt with me. I am not sure I want to get married again, so he says he’ll settle for a commitment ceremony.

One of the things I love about him is that he is so accepting of who he is and hides nothing about himself; and his family and friends accept him exactly the way he is. I, on the other hand, feel like I’m hiding myself from my family at every turn.

My question is: How long can a relationship with such disparate backgrounds last?

I haven’t told my parents because they haven’t gotten over my divorce and are very protective of me and don’t want to see me hurt, and he is so different from anyone I’ve ever been with; my friends think I’m ‘rebelling’ after my traumatic divorce.

I know he is hurt that I don’t tell my parents about us, or bring him around, I keep feeling like once he has a full-time job I can gloss over the not-so-nice stuff in his background, and ‘groom’ him to be acceptable to my family but I know that’s not fair to him. If he accepts himself, why can’t I?

He always says, “I’ll always be blue-collar, baby!” On the other hand, his father is a private-school teacher and his mother is a nurse. His sister and brother-in-law are also teachers. I know deep-down he feels insecure about that, but I think he’s scared to try for something better because of his record, and I think he has a fear of failing.

I am so torn; do I keep going, trying to see where this will end up? Do I end it because he’ll never be ‘good enough’ for my friends and family? What about the financial factor? If he never has a decent job, can I be the breadwinner and he the stay-at-home parent? Will that ever be acceptable to him, me, and our families? Do I support him and push him to better himself or just accept him as he is?

I’m looking for some perspective because obviously, I have lost all of mine…

Avery: Wow. I really feel for you. This is one of the most difficult questions that I’ve ever seen at “Ask Real Guys” and there’s no easy answer. Family pressures can be so great, and even though this guy seems so right for you on so many levels, the way he’ll be accepted / not accepted by your family can really weigh on someone – especially when you come from a family where culture is so important.

I think that you should continue with this man for a while to see if his actions and thoughts are truly genuine. If you really feel that he is the right guy for you – in your heart – then maybe first approach your siblings to get their take. Going to them first may help you move in the direction of talking to your parents. Also, since you were married once and went through that painful situation, it’s conceivable that at some point your parents will opt for your happiness first, instead of trying to find the “perfect” situation (whatever THAT means). I really see how tough these decisions are for you but I can tell by your question that you are an extremely intelligent and savvy woman, and I know that in due time, the right answer for you will present itself. Take it slow and the best decision for you will be more easily discovered.

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