Wedding Planning Red Flags: What a Divorce Attorney Wants Every Bride to Know Before Walking Down the Aisle

Planning your dream wedding should be one of the most exciting times of your life, but what if I told you that how you and your partner navigate the planning process could reveal crucial insights about your future marriage? On this week's episode of The Pre Nup, I sat down with Alan Feigenbaum, a top New York-based divorce attorney, to discuss the wedding planning red flags that every bride should watch for — and the hard truths about marriage that no one talks about during engagement season.

While my hope is that every marriage lasts forever, Alan's decades of experience handling divorces have given him unique insight into the patterns that lead relationships to fail. His advice isn't meant to scare you away from marriage, but rather to equip you with the tools and awareness you need to build a stronger foundation with your partner. Consider this your relationship reality check before you say "I do."

The Communication Test: How Wedding Planning Reveals Everything

Wedding planning is essentially a stress test for your relationship, and according to Alan, the biggest predictor of future marital problems is breakdown in communication. "The pattern I see, which is like a broken record, is that communication tends to breakdown and we all kind of form an opinion in our own minds of what the other person or partner is thinking without ever speaking to them about it," he explains.

During wedding planning, you'll face countless decisions together — from budget allocation to guest lists to vendor selection. Pay attention to how you and your partner handle disagreements during this process. Do you talk through issues openly, or do you shut down? Does one person always get their way? Are you making assumptions about what your partner wants without asking?

If you can't communicate effectively about wedding flowers or seating arrangements, how will you handle the truly challenging conversations that marriage brings — like finances, career changes, or family planning? The couples who struggle most in Alan's practice are those who stopped talking to each other long before they reached his office.

Financial Red Flags That Start Before the Wedding

Money is one of the leading causes of divorce, and wedding planning often provides the first glimpse into how you and your partner handle finances together. Alan warns about "financial coercive control" — when one person holds all the financial cards and the other operates with limited knowledge or agency.

Watch for these financial warning signs during wedding planning:


"Years and years can go by and then you really don't have that financial independence," Alan notes. "You have a veto power. One person is saying can I spend this? Can I buy this? No, not today. That's scary territory to get into because then you no longer have control over your life."

Healthy couples should be able to discuss wedding budgets, contribute according to their abilities, and make financial decisions together — even if one person earns significantly more than the other.

The Prenup Conversation: A Relationship Litmus Test

While not every couple needs a prenup, Alan believes every couple should understand what marriage means legally and financially. "I would rather that instead of do you have to have a prenup or not have a prenup, I preferred if people knew that when you divide up marital property in New York, it's called equitable distribution."

The conversation about whether to get a prenup — not necessarily the prenup itself — can reveal everything about your relationship's health. Can you discuss difficult "what if" scenarios without it turning into a fight? Are you both willing to protect each other's interests? Can you separate the practical from the emotional?

"If you cannot talk to your partner [about difficult topics], I mean they're not easy discussions, but you have to be able to talk about the hard stuff," Alan emphasizes. "If you can't deal with the conversation in hypotheticals, that's a problem."

Prenups make the most sense for couples with significant assets, business interests, or those entering second marriages. However, the ability to have mature conversations about money and future planning is essential for every couple.

Family Dynamics and Boundary Setting

Wedding planning often brings family drama to the surface, and how you and your partner handle outside pressure can predict future marital challenges. Alan frequently sees cases where "emotional abuse sometimes from in-laws" contributes to divorce.

During wedding planning, notice:


The couple featured in our premarital counseling segment faced pressure from family to delay their wedding planning until the bride's older sister got engaged first. This type of family interference, while it may seem minor, can set problematic precedents for your marriage if not addressed directly.

Strong couples present a united front to their families and make decisions based on what's best for their relationship, not what keeps everyone else happy.

Age Gap Considerations and Life Stage Alignment

Alan points out that significant age differences can create challenges that aren't apparent during the honeymoon phase: "At the time of a marriage, let's say one is early 20's, the other is 50. All's well and good, but then when the 50 year old is pushing 80 and needs depends, the 20 year old loves skiing and playing tennis."

Even smaller age gaps can create issues if you're at different life stages. During wedding planning, consider:


These conversations might not feel romantic, but they're crucial for long-term compatibility.

The Aftermath: Understanding the Real Cost of Divorce

While no one plans to get divorced, understanding the realities can help you make more informed decisions about marriage. Alan explains that even amicable divorces are expensive because "you're almost creating two families under this one umbrella. So now there's going to be two households."

Beyond financial costs, divorce involves:


In New York, spousal support typically goes to the "non-moneyed spouse" — often someone who left their career to raise children or support their partner's ambitions. The financial impact can last decades; Alan mentions a client who paid spousal support until his ex-wife passed away when he was in his 80s.

Key Takeaways

FAQ

What are the biggest red flags during wedding planning that predict divorce?

The biggest red flag is inability to communicate effectively about decisions and disagreements. If you can't talk through wedding planning challenges together, you likely won't be able to handle bigger marital issues. Other major warning signs include financial secrecy, family boundary issues, and one partner consistently dismissing the other's concerns or preferences.

Should every couple get a prenup before marriage?

Not every couple needs a prenup, but every couple should understand what marriage means legally and financially in their state. Prenups make the most sense for those with significant assets, business interests, or entering second marriages. However, the ability to discuss difficult financial topics openly is essential for all couples, regardless of whether they ultimately sign a prenup.

How can wedding planning reveal financial compatibility issues?

Wedding planning often provides the first major test of how couples handle money together. Red flags include one partner making all budget decisions unilaterally, lack of transparency about finances, unwillingness to discuss money openly, or significant disagreements about spending priorities that can't be resolved through communication.

What should I do if my family is interfering with my wedding planning?

You and your partner need to present a united front and make decisions based on what's best for your relationship, not what keeps families happy. Have honest conversations with your parents about boundaries, and ensure your partner supports you when their family creates problems. How you handle family interference during wedding planning sets important precedents for your marriage.

How expensive is divorce if a marriage doesn't work out?

Divorce costs vary significantly based on how contested the proceedings are, but even amicable divorces are expensive because you're essentially creating two separate households. Beyond attorney fees, there are costs for dividing assets, potential spousal support payments, and the practical expense of maintaining separate homes. In some cases, spousal support can last for decades, particularly when one spouse gave up career opportunities to support the family.

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This post is based on an episode of The Pre Nup: A Wedding Planning Podcast. Follow us @the_pre_nup on Instagram and TikTok, and listen wherever you get your podcasts.