When was the Last Time You Spoke to Your Parents or Siblings? Being estranged from family can be (and I said CAN BE) a huge red flag, y'all. When was the last time they talked to their family? Do they have strained relationships, or have they "blocked them out" of their lives? Not having a good, healthy relationship with family can be a sign of a toxic personality disorder. IT CAN BE- not always. Sometimes, under certain circumstances, cutting family out is the only way to live.
How Did Your Last Relationship End? Let's cross our fingers and toes here and hope they say something kind about their ex and the breakup. If not, listen closely to how shit went down. Do they take accountability for their role in the breakup, or do they blame their ex? If it's the latter- run, and run fast.
Do You Believe in Happily Ever After? Yikes. This is kinda a trick question, especially when it's a guy doing the asking. If they say YES, they may have false expectations of what a real relationship is supposed to look like. Remember, this isn't a fairy tale. Relationships take work, hard work...and if you go into your marriage thinking it's going to be all sunshine and rainbows, you are in setting yourself up for a big-fat thunderstorm.
If you Could Change One Thing About Your Life, What Would It Be? Ummm...if it's "I'd still be married to my EX," that's a bad sign. Or, "Wish I didn't lie about blank." Hopefully, they say something along the lines of, "I wish I took that job in Houston" or "Should have traveled after college." Yes! Those are great ones. Phew!
Are You Over Your Ex? This is a biggie, and I recommend asking this on the very first date. It should be an easy, fast answer. No biggie. If they are still resentful, angry, and bitter, chances are they have not- red flag. Wait, wait. While bashing an ex on a date is a red flag in my book...explaining your past relationship in a calm, mature way is necessary and understandable.