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How can I know if my daughter's boyfriend really loves her?

The question

My daughter is in a serious relationship with a gentleman who is 13 years older than she is. She thinks marriage is in their future and is expecting him to ask me for permission to marry her. What questions might I ask him prior to giving my approval to best demonstrate that he is a man who deserves my daughter and will respect her needs and nurture her ability to be independent?

The answer

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Well, first of all, be happy that he wants to "ask your permission" before marrying your daughter. Old school! Maybe it helps he's a bit older, and not part of the millennial hang-out/hook-up culture.

Writer Kate Bolick recently created quite a stir with an Atlantic article declaring the reason she hadn't married yet, at the age of 39, was because modern men are either "deadbeats" or "playboys." The saddest part of the article, to me, was when she described a group of women who were recent college graduates. She says that "these denizens of hook-up culture were far more experienced than I'd been at their age," and at first "they all joked easily about sexual positions and penis size … with the offhand knowledge only familiarity can breed."

But when Ms. Bolick asked them how they felt about the prospect of being single into their 30s, like her, there was a long pause, then: " 'I don't think I can bear doing this that long,' one of them said, with undisguised alarm."

I'm not saying everybody should get married. But I am a fan of the institution (smartest thing I ever did), and I think it's cause for celebration that your daughter has found someone she wants to marry, who wants to marry her, and is leaving "hook-up culture" behind, at least for a time.

I mean, sure, sit the guy down, have a beer and some pretzels, and get to know him. I guess in your shoes I'd be curious to know a) what his plans are for the future in his career, b) what it is that he loves about your daughter.

Not that the specifics matter so much: What you're looking for in both cases is passion, a fire in the belly. My own father-in-law, 20 years ago, never sat me down like that – though he could have. I was braced for it: After all, he comes from a generation, raised in the shadow of the Depression, lived through a world war, that valued economic stability above all else. And here was his daughter marrying this … writer?

If he had, I could have delivered a soliloquy that would have singed his eyebrows. I had it all ready. It begins: "Well, Wilson, let me tell you, first of all: I'd gladly take a bullet for your daughter, any day of the week – okay, maybe gladly's a stretch, but if someone were to pull a gun on her, would I jump in front? In a heartbeat. And as I slid down the wall, leaving a bloody track, I'd smile quietly to myself, knowing I'd done the right thing …"

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Then I'd explain my burning ambitions to claw my way to the top of the writing game, in order to provide a happy life for his daughter and future grandchildren, and so on and so forth.

So yeah, maybe look for a bit of that in your prospective son-in-law. What a career needs at the beginning is purpose and ambition; what a relationship needs is momentum. Conversely, the father-in-law/son-in-law relationship is one best eased into, like a hot tub. So steer clear of any formal inquisition or hackle-raising interrogation this early on. Try to keep everything on a friendly footing, at least at first. He's much more likely to open up to you that way anyway.

And I wouldn't worry too much about whether he "deserves" her or not. I mean, what man in the history of humanity has ever deserved the woman he's with? Did you deserve the mother of your daughter? Exactly. Better if he doesn't deserve her and knows it. That way, he'll spend a lifetime trying to impress her.

That said, a couple of other things I think are important in the early going are: good impulse control, and that he loves her for her faults, rather than despite them.

If you detect poor impulse control, then you have my permission to speak to your daughter in the strongest and most strenuous terms. Otherwise, I would just, tactfully, with great caution and circumlocution – remember, it's an IED-filled road to go down, criticizing someone's fiancé! – share your findings with your daughter, but take it no further than that.

Because what's all this about "permission" anyway, and who says she needs it or will abide by your ruling? Even if she were such a dutiful daughter that she called off her wedding because you withheld your "permission," then who's the one not "respecting her needs" and "nurturing her ability to be independent?"

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