DATING FORUM

Question

I went out a few times with a guy who I really liked. Then I found out from one of his close friends that he recently lost thousands of dollars in sports gambling. He usually doesn’t lose, but the one time that he did it was major. When I asked him about it, he said it was no big deal. Now I’m worried because he always buys expensive clothing at least every week and I don’t think he earns that much. I spoke to a girl he once dated and she told me that he’s very impulsive and when he gets irritated, he can say not nice things. I want you to know that he’s super sweet to me. He takes me out nicely and buys me cute little tchotchkes. He treats me like a princess. What do you think about such a guy? Even if he has a problem, is it possible that he got better?

Response

In a world where people complain about being ignored, ghosted, or treated carelessly, the kind of attention he gives you feels like gold. This is the kind of modern dating story we don’t like to question because on the surface, it looks too good. It begins like a fairy tale and quietly starts dropping clues that it’s not. And if your gut is already asking questions, you already know the answer, but here’s the validation you need from my response.

You wrote. “He treats me like a princess.” “He’s super sweet to me.” “He takes me out nicely…buys me cute little tchotchkes.” This is the same guy that lost thousands of dollars gambling but says it’s no big deal. He’s also impulsive, buys things he likely does not even need, and gets nasty when he’s angry. That’s not background noise. That’s the story of who he really is, and deep down, I think you already know that.

How someone treats you when everything is going well is not the test. It’s the baseline. Because real marriage is not built on candlelit dinners, sweet words, and “cute little tchotchkes.” It’s built on stress, pressure, money decisions, various family tensions, and anything that life throws at you when you least expect it. Who is this guy when he’s frustrated, and when he doesn’t get what he wants? Is that when he gets nasty?

His personality is not the only issue you need to figure out. There’s another big concern called gambling addiction, which is exactly what I think it is based on the way you are describing it. He can say that it’s no big deal all he wants, but losing “thousands of dollars” at sports gambling is not a personality quirk. It’s not a hobby, or just “boys being boys.” It’s a wildly flashing red warning light. What I find frightening and what should be even more worrisome to you than the gambling itself is his response: “It’s no big deal.” That sentence tells you more than the monetary loss ever could. Because an emotionally healthy person who has confronted a problem speaks differently. If he had said, “Yeah, I messed up, and I’m working on it,” shows he’s growing in a positive way, and we could cut him some slack. But a person who shrugs it off is in denial. In fact, he could be gambling away his money and other people’s money right now. This is serious.

Furthermore, his spending habits don’t seem to stop with gambling. You mentioned that he buys expensive clothing every week. That’s not just being a good dresser. That’s a pattern. Gambling plus impulsive spending is a lifestyle pattern of chasing feelings. The high he feels off a win and the thrill of a purchase, along with that temporary feeling of success until it wears off, and then it starts all over again. A man who needs to constantly feel like he’s winning will eventually make decisions that cause real losses. And in marriage, those losses become yours too.

You’re feeling conflicted, because, as you say, “He’s so sweet to me.” Here’s what you need to understand: People are not one-note characters. Someone can be charming, attentive, generous, and also impulsive, financially reckless, and verbally hurtful when triggered. The question isn’t which version is real. The question is: which version shows up under pressure? Because that’s the version you’ll be married to!

Could he have gotten better? Can he get better? The answer is yes. Can he completely change? Of course, people can change. But real change is not a feeling you pick up on. It’s not his charming self that he portrays to you. It’s not a softer tone of voice. It’s not a good few weeks of living by the book. You need to find out if he stopped gambling entirely. Has he put financial boundaries in place? Has he worked on his anger? Has he taken responsibility for how he treats others? If the answer is “I think so” or “he seems better,” that’s not evidence. That’s hope, my friend. And hope is beautiful—but it’s not a strategy for marriage.

I need to circle back to where you wrote “He treats me like a princess.” That is the most important line in your letter. Because being treated like a princess is not the goal. Being treated with consistency, stability, and emotional safety is. A man who buys you gifts but can’t regulate his anger will eventually use words that no gift can erase. A man who spends freely but minimizes financial recklessness is not generous—he’s unstable with money.

This is not about whether he’s a good guy or a sweet guy. It’s about whether he’s a reliable marriage partner. Can you trust him with a shared bank account? Can you trust him when he’s angry? Can you trust his judgment when life gets hard?

We don’t need more fairy tales in dating. We need clearer vision. A man who makes you feel like a princess is not automatically a good partner. Speak to the many divorced people out there who were treated like you were during their courtship, but experienced sheer terror while married to the same person. In fact, some have described their ex-spouse as Jekyll and Hyde. The sad reality is that in many cases, these people refused to look beneath the surface and ignored all the red flags. A relationship that feels magical in calm moments, but uncertain when you look deeper, is not something to romanticize. It’s something to examine. Closely.

It’s comforting to believe that there are two versions of a person: The good one you experience, and the bad one you’ve heard about. But that’s not how people actually work. There aren’t two separate personalities. There’s one person with patterns that show up under different conditions. When everything is going right, many people can be extraordinary because nothing is challenging them. But remove those ideal conditions and something else emerges. Not a different person. It’s the same person…without the filter. You are not choosing between two versions. You are being shown the full range.

Add to the report that he can become cutting or harsh when angry, and a clearer picture starts to form of a person who may struggle with limits—financially and emotionally. Someone who feels deeply, reacts quickly, and minimizes the consequences can also be incredibly kind when everything is going his way. That’s exactly the point. Where does that leave the person on the receiving end of the “princess treatment?’ Conflicted.

You don’t marry the best version of someone. You marry their patterns. When you get married, you are marrying the full package. That’s a very important point that I wish singles would focus on while dating. Don’t date someone for who they are on their best behavior when life is going well for them. Date them for their patterns. Right now, his patterns are telling you that he minimizes serious issues, chases impulses, and may not be able to handle anger well. And the most dangerous part? He looks really good while doing it. I will leave you with this. A man who makes you feel like a princess on Tuesday, but unstable on Thursday, is not a fairy tale or a love story. He’s a risk profile. It’s whether you’re willing to build a life on that kind of uncertainty. 

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis and shidduch consultant. Baila also produces and hosts The Definitive Rap podcast for 5townscentral.com, vinnews.com, Israel News Talk Radio, and WNEW FM 102.7 FM HD3, listenline & talklinenetwork.com. She can be reached at [email protected].