Welcome back to Tough Love with Abigail Shrier, the new advice column from The Free Press! Every Thursday, our contributing editor will address your conundrums, with no hesitation and no sugarcoating—just straight-up Tough Love. This week, Abigail answers a mother who really doesn’t want her 22-year-old daughter to get married. To receive Tough Love directly in your inbox, every week, sign up here.

Dear Abigail,

My daughter loves love. She recently got engaged to her college boyfriend (they’d been dating less than a year before the engagement), and they are going to get married right after graduation, when they’ll both be 22 years old. They both have good-paying jobs lined up but will be spending the first couple of years after graduation apart as they complete the training/education needed for their jobs.

I can’t help but worry that they’re too young to get married. I also worry that she’ll end up making choices based on the relationship that will derail her training/education for the job that she has lined up, which is essentially her dream job. At 22 years old, I want her to focus on her career and, if I’m honest, grow up a little more.

Here’s the rub: I got married at 22 myself. But that was in the ’90s. And I am from Wisconsin, where that was pretty common. My brother got married at 22 also, within a year of graduating from college. However, my marriage ultimately failed. We stuck it out for more than 12 years and had three kids along the way but, by the end, we didn’t love each other anymore. And he cheated.

Also, before we got married, we agreed that he would choose my career over his, even if it meant that he would be the primary caregiver for our future children. This was a promise that he ultimately refused to keep. And it’s the same promise that my daughter’s fiancé is making to her now. But I just know that the fiancé can’t possibly understand what he’s promising. He doesn’t know what it will be like to be married.

One more issue—my daughter is very ambitious, successful, attractive, smart, and fun. She has always had a boyfriend, and she told me that three of the others proposed. But, given that these two are facing certain separation for a couple years, I feel like her fiancé proposed in order to tie her down. To take her off the market.

I want my daughter to be happy and to feel loved at all times. I want grandkids someday. I know, in my head, that just because my marriage failed, other young marriages succeed. (My brother’s has.) But, in my heart, I’m having a hard time feeling happy for them. Right around the engagement, she and I had a long, hard conversation, and I told her my concerns. At this point, I’ve shifted to the supportive and paying-for-the-wedding mom, but it’s hard not to worry that I’m enabling a big mistake. Do I have one more hard conversation with her? Or with both of them? Or do I just cheer them on and keep my concerns to myself and prepare myself to help pick up the pieces when they grow apart?

—Lisa, 50, California

Dear Lisa,

A few months before I was due to get married, a rabbi gave my soon-to-be husband and me a talk. “In my decades in the rabbinate,” he said to us, “I’ve seen couples who looked like they were matched by God and also couples who looked like they were barely going to make it to the wedding canopy.” Over the years, he’d had occasion to be surprised for both better and worse: divorces he hadn’t seen coming and long, happy marriages where he’d doubted the wisdom of the union.

The only difference between the two groups that he could identify was time...