9 Questions To Ask On A First Date, According To Divorce Lawyers

Avoid a bad end by asking the right questions at the start.
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Few people have a keener eye for relationship red flags than divorce attorneys. They’ve seen firsthand how quickly personality quirks can turn into major annoyances and the problems that can lead to calling it quits.

That also makes them surprisingly good at giving dating advice. Below, family law attorneys from across the country share nine pointed questions to ask on a first date if you want to avoid getting into a relationship with someone you’ll eventually divorce.

1. “When was the last time you talked to your siblings or parents?”

“I would find a way to ask your date about how close they are to their family. I see many divorces caused by one person being so close to their family that they prioritize them over the marriage and have poor boundaries: Once you are married, your marriage has to be protected and prioritized over the relationship you have with your family of origin. On the flip side, bad family relationships can be a sign of personality disorders and an inability to sustain relationships in a long term way.” ― Carla Schiff Donnelly, a divorce attorney in Pittsburgh, Pennsylvania

2. “Do you believe in happily ever after?”

“All relationships require work and commitment from both parties to make them work. Someone who thinks ‘happily ever after’ just happens is probably not going to be a great partner.” ― Katherine Eisold Miller, a divorce attorney in New Rochelle, New York

3. “Are you married?”

“Seriously, ask this. Separated or married means not yet divorced. Your date should be divorced.” ― Randall Kessler, a divorce attorney in Atlanta, Georgia

4. “What do you love most about your job?”

“Ask about their work: Do they have a sense of pride in what they do? Are they passionate about it? Or do they go from job to job? Conversely, are they married to their job and have little room for staying in bed on a cold Sunday morning, or traveling to exotic places, or even 20 minutes to the movie theater without constantly looking at their emails? That’s a red flag.” ― Lisa Helfend Meyer, a divorce attorney in Los Angeles, California

5. “Where did you go on your last vacation?”

“What you really want to know is ‘How did you pay for your last vacation?’ but that is a hard question to ask outright. But if your date went on an extravagant vacation, you could innocently probe further with a ‘Wow, how did you pay for that?’-type question. Finding out if your date made a large purchase by saving over time or putting the trip on a credit card can be very useful information. It can lead to information about how much debt your potential mate has and their general attitude toward debt and money in general. Money problems are one of the primary causes of marital problems. Understanding how your date views and handles money before you walk down the aisle is critical to long-term marital happiness.” ― Carolyn C. Van Tine, a divorce attorney in Boston, Massachusetts

6. “Do you know who Johnny Carson is?”

“Basically, find a way to ask your date how old they are. Many of our divorce clients swear they had no idea how young or old their spouse was until after they were engaged.” ― Randall Kessler

7. “Do you consider yourself a good communicator?”

“Communication is so important. Oftentimes, the cause of the breakdown of the marriage is an inability to communicate. If people aren’t telling each other what bothers them (and how to fix it), it can create resentment that grows over the years, causing the parties to drift apart until they are so far apart there is no chance they can get back together. Learning how your date communicates and figuring out if that method of communication works with your own is a great first step in establishing a solid foundation and avoiding divorce down the road.” ― Carolyn C. Van Tine

8. “How did your last relationship end?”

“I would ask them how their last relationship ended. If their explanation is all about how it was the other person’s fault, that would indicate a red flag. Look for someone who is willing to take some ownership of the relationship’s failure. It shows their humility, honesty and ability for personal growth.” ― Carla Schiff Donnelly

9. “If you could go back in time, what’s the one thing you would change about your life?”

“This is a fun conversation and it can reveal a lot: Ask each other what you’d do differently if you could go back and do it all over again. ‘I would live in a country far away from my mother’ is a bad sign. ‘I would have gone to college on the East Coast because I never had an opportunity to live there’ is probably not a bad sign. ‘I would have pursued acting or become a doctor’ is probably not a bad sign, unless the person is very discontented with their work. ‘I should have married my high school sweetheart, with whom I still stay in touch’ is a very bad sign.” ― Lisa Helfend Meyer

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