DEAR EMILY,

Twenty years ago, I devised a way to get rid of an eight-year-relationship that my mom objected to. She was my high-school girlfriend, smart and pretty, but from a lower income status, and whose parents were nobodies in the social circle I grew up in.

I am pretty sure Mom harassed her no end. She remained silent throughout all the time she was with Mom and me. She moved out of the country, married and had kids.

Now, she’s back and my heart is singing; I sleep with a smile on my face. I see her often—from a distance—and have been tempted to contact her through mutual friends. But I’m married with kids of my own. My wife has a slight resemblance to her, is far richer and well-connected; I thought that would make for a good marriage. Our family is well-respected in society, and we have built a fortune beyond our expectations.

Yet, I long for those tender moments, the pureness and simplicity of young love. It was she who gave me the most by giving me herself, and I am ashamed and deeply regretful of what I had done to her. Now, I am scared that on my deathbed, I will not have her by my side. I want to see her, talk to her. I might not have enough strength to stay away from her.

—Stand by J

“Devising” something to rid yourself of a girlfriend of eight years sounds so ruthless. Just because your mother objected to her? Was the whole rationale for this self-inflicted unhappiness just economics? How terribly materialistic of mother and son, don’t you think?

Instead of flushing her out of your life, you could have lifted her out of her “nothingness” by making good use of your education and building your fortune from scratch, with this woman beside you helping every inch of the way. This would have made your love real, and given your mother an honorable lesson in life.

Now, look what it’s done to you. Though you married the right girl with all the right credentials, you never found the happiness you had with this impoverished girl who came from nothing. Clearly, money, in spite of its potential to buy anything and everything, does not hug back or give you that inner contentment that spells true happiness.

If she had remained poor and you saw her selling vegetables past their due date by the wayside, surely, you won’t be having this problem. You would have walked on nonchalantly and thought nothing of it. Why is she then suddenly so desirable to you? Has she now become your equal in status? If so, then you really haven’t grown up and matured. You are still attracted by riches!

Had you said you’ve regretted not being with her all these years and want her forgiveness for being the creep you’ve been to her, even the heavens will probably smile and take cognizance of your suffering.

Which is it then?

Ask her out for coffee if this will help you lighten your anxiety a bit. She might go out with you just to show you what you’ve missed. You say you may not have the strength to keep away from her—but what if there’s a complete twist of fate this time? What if poetic justice kicks in, in her favor? What will you “devise” then?

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