My Boyfriend Wants a Prenup. Can I Say No?

I have been dating my boyfriend for three years; we’ve been living together for two of them. Last week, he said we should get married and that he wants a prenuptial agreement. I have always paid my way in our relationship, so I was surprised by this. He has more money than I do, but it’s not exorbitant, “Succession”-type wealth. I agreed to his request because I was taught to be financially independent, but now I resent him for it. I’m nervous about what’s to come rather than excited to get married. Can I push back on this?


Were there any hearts and flowers in your boyfriend’s marriage proposal, or was it all prenup? I get it if you buried the romantic bits because you’re distraught by the financial proposition. But if there was no sweetness in it: Red flag! Otherwise, let’s dig into prenuptial agreements, which are less scary than many people think.

About 40 percent of marriages end in divorce. That’s scary! So, whether your boyfriend managed to save $50,000 or inherit $50 million (still chump change for the nepo babies on “Succession”), I understand his impulse. Asking to protect his premarital assets and divide those you create together, which is largely in keeping with divorce law, doesn’t make him a doomsayer about your relationship any more than buying fire insurance makes him an arsonist. Stuff happens — about 40 percent of the time.

Now, let me add that I am not generally a fan of prenups for people without big assets or liabilities, or children from previous relationships. (Yes, I am looking at you, medical school debt!) Life is unpredictable. One of you may hit a career jackpot. Or parenthood may depress a spouse’s earnings. But these things may not happen for years — if at all. Complex prenups that divide assets before they exist or cap support payments before there’s a track record of earnings are silly — and often unfair to the poorer spouse. So, ask your boyfriend what he’s worried about, and then hire a lawyer and hash it out. Don’t be bullied into a prenup, though: You can’t marry the guy if you can’t agree on what’s fair.

Through a series of unfortunate events — including drug misuse and a moving vehicle — my brother is in jail awaiting trial. It’s a mess! The problem: Our mother recently moved into an assisted-living facility. She is just getting acclimated; she also just asked about my brother, who normally visits her. He wants me to help arrange a phone call with her, but I don’t want to do that unless he promises not to mention his legal troubles. I think it would be too upsetting for her. My brother refuses to make that promise. What should I do?


I know you want to protect your mother, and I respect that. But you haven’t shared anything that entitles you to control her relationship with your brother — a heart condition, for instance, or an anxiety disorder. Consult with a therapist at her facility about the possible effects of your brother’s news or arrange for him to have that conversation. I’m sure his situation will upset her. Don’t assume your mother can’t handle it, though, simply because she needs some help with daily living.

I bumped into a neighbor in the lobby of our building. I hadn’t seen her for a while, but it was obvious she had undergone extensive cosmetic surgery. Not to be judgmental, but I can’t imagine she thinks no one notices. I felt uncomfortable having a conversation without first addressing the elephant on her face. And it seemed disingenuous to say: “You look wonderful! What have you done?” How would you handle this?


Cards on the table: I am appalled by your question, though I’m sure you are sincere. By your own account, this woman is an acquaintance whom you bump into occasionally, not a close friend. Why on earth do you feel entitled to comment on her appearance, much less claim that it’s a prerequisite to other conversation?

Unless neighbors ask you specifically about their changed appearance, say nothing. As for conversation starters, go anodyne: “I haven’t seen you in ages! How are you?” Our acquaintances know if they’ve had cosmetic surgery. They don’t need us to tell them.

After years as a homemaker, I finally found a job I was excited about and announced it proudly to family and friends. But the job turned out to be a major disappointment, and I quit six weeks later. I haven’t told anyone because I’m embarrassed that it fizzled so quickly. Now, people are asking about my exciting new job that I left weeks ago. It’s getting uncomfortable. What should I say?


Go with the truth: “It didn’t work out.” And stop beating yourself up. You are hardly the first person to be disappointed by the realities of a shiny new job. Now, I don’t know the nature of your disappointment, but no job is perfect, and six weeks is an awfully short period. So, keep in mind — for next time — that patience and negotiation can sometimes work better for us than heading out the door at the first sign of trouble.

For help with your awkward situation, send a question to [email protected], to Philip Galanes on Facebook or @SocialQPhilip on Twitter.