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.