Divorce Lawyers Recommend Asking These Questions On A First Date

Divorce lawyers may not be relationship experts, but they have picked up a thing or two about the factors that lead up to a failed marriage. Because of this, they may actually be the best people to go to about dating. Here are nine questions they suggest asking on a first date to determine whether a relationship is worth pursuing.

  1. “Which box do you check for status on forms (single, married, etc.)?” This might be an obvious one, but unless your date’s status is strictly in the “single” or “divorced” category, don’t schedule a second date, says Georgia attorney Randall Kessler. Any other situation is messy, complicated, and filled with drama—something you definitely don’t need in your life.
  2. “How old are you?” This question might seem a bit forward, but Kessler revealed that many of his clients claimed they didn’t know the age of their partner until after they were engaged! Many people are inclined to lie about their age, so you can even ask them indirectly by referencing pop culture. A conversation about your favorite movies, television shows, and music can give you the answer you’re seeking and can help you learn about your date’s interests.
  3. “How close are you to your family?” Family ties can reveal a lot about your date, according to Pittsburgh attorney Carla Schiff Donnelly. If he’s too close to his family, that can be a red flag. He may have boundary issues or be too dependent on them. Nobody likes a mama’s boy. If he’s at odds with his relatives, it can indicate that he has a personality disorder or that he has a hard time holding onto relationships. If you don’t want to get too deep on the first date, simply ask, “When was the last time you spoke to your parents (or siblings)?” It may just spark a conversation that sheds some light on his situation (and give you a chance to share your own).
  4. “How did your last relationship end?” You should definitely note what he says and how he says it. Schiff Donnelly points out that if he places all the blame on his ex, he can’t take responsibility for his own actions and mistakes, which is not a good quality in a partner. You should also pay attention to how he says it. Is he bitter? Does he miss his ex? Did he dump her over something small? It’s also probably a good way to determine if you’re his side chick; if he tells you all this and gets caught in a lie, you might not be the only non-platonic woman in his life.
  5. “What’s your favorite thing about your job?” Since we spend half of our time at our jobs, they become an important part of our lives. Los Angeles attorney Lisa Helfend Meyer suggests that your date’s attitude about his job can indicate how a potential future with him might pan out. For example, does his job matter more to him than his relationships? Does he take pride in what he does? Does he like his job? If he’s always coming home complaining about it but isn’t interested in making moves to change his situation, it may affect your dating life in a negative way.
  6. “Is there something about your life you would change given the opportunity?” You can pose this question as a fun game, but Helfend Meyer predicts that his answer can tell you a lot. For example, if he says he wouldn’t let his high school sweetheart get away, it could mean that he’s still hung up on her. Some answers can be innocent and not point to any potential problems, but some could raise some very scary red flags. Use your best judgment to figure out which is which.
  7. “Do you believe in happily ever after?” Happily ever after doesn’t exist in the real world. Love is not this beautiful, idyllic phenomena; it takes work, and it can be dirty and complicated. Someone who thinks a relationship will last without any effort is probably not the best person for you. Having realistic expectations for a modern relationship is a must, according to New York attorney Katherine Eisold Miller.
  8. “Do you think you’re a good communicator?” Lack of communication is one of the (if not the) major causes of divorce. We’re all so afraid to say what bothers us, and the resulting resentment can grow and grow until it explodes like the proverbial atom bomb in the long run. Figuring out how your date communicates can help you see if your way meshes well with his. Otherwise, it will be very hard to maintain a healthy relationship, says Boston attorney Carolyn C. Van Tine.
  9. “Where was your last vacation?” While seemingly random, this question can tell you a lot about how your date handles money. If you find it uncomfortable to ask your date about his finances outright, this question is a more innocent way to probe. What you really want to know with this question is whether or not he saved up the money to splurge on that luxury vacation to Aruba he took last year or just put it on a credit card and called it a day. You can then use this question as a segway into discussing debt and money in general, Van Tine suggests. Money problems are another central issue that leads to divorce, so you’ll want to know where he stands from the beginning.
Ginnifer Bronstein is a freelance writer from New York. She enjoys writing about relationships, entertainment, and fiction. Her goal in life is to travel the world and be an accomplished writer, but she'll settle for stopping and smelling the roses.