First Date Questions To Ask Him To See If He’s Worth A Second

So you’ve been set up or you’ve found someone you like and you’re going out on a first date. You’re excited about getting to know this guy, but you also don’t want to devote more time than is necessary to someone who just isn’t right for you. Does he deserve a second date? Here are some interesting questions you can ask him the first time you go out to see if there’s a chance things could work out between you.

  1. When and why did your last relationship end? You obviously don’t want to start dating a guy who just recently broke up with his girlfriend or separated from his wife. He’s still going to be carrying a lot of baggage from that and might not even be over her yet. If he throws all the blame for the relationship falling apart on his ex, then you know he’s the kind of person who doesn’t admit his faults or take responsibility for them.
  2. What are you looking for right now? It’s better to talk about your expectations for the relationship before diving headfirst into it. Is he looking to date casually or does he want a serious and committed relationship? It’s probably not a good idea to go on a second date with a guy who’s not on the same page as you. Discussing this can save you from misunderstandings and hurt feelings down the road.
  3. How is your relationship with your parents? A person’s relationship with their parents can give you a lot of insight into how they think about love and relate to people. Keep in mind that not having a good relationship with his parents does not mean there’s something wrong with him. Just pay attention to how he talks about them and the reasons he gives for the crappy connection he has with them.
  4. What’s your biggest relationship deal-breaker? Talking about your dealbreakers on the first date might seem too intense and personal, but it can tell you a lot about your potential partner. If his dealbreaker is too flimsy or it feels like he’s asking too much, you’ll know on time and move on, rather than wasting his time and yours.
  5. How do you spend your free time? What does he like to do on his off days? Would he rather go hiking, clubbing, or stay indoors and have a gaming marathon? What’s his idea of fun? This question is a great way to find out whether you have common interests. If your hobbies are compatible, that’s all the more reason to go on a second date.
  6. What qualities do you want the most in a partner? The beauty of this question is that it exposes the guy’s good and bad traits. If he says that honesty is important to him, that’s a sign that he considers himself to be an honest and faithful person. If he says wants a partner who can give him space, that might mean he’s not very sociable. Or that he wants the freedom to neglect his partner without being called out on it. A guy who can’t list any qualities has no idea what he wants and might not be mature enough to handle a serious relationship.
  7. Is there someone that might think they’re in a relationship with you? This is one of my favorite questions and it almost always elicits a laugh. Sure, he might not be in an official relationship, but he might have a complicated thing going on with someone. If he says, oh there’s this chick who wants something more with him but he’s not dating her, that could mean he’s stringing her along until he finds someone better.
  8. What makes you happy? This is going to lead to a great conversation. Everyone enjoys talking about the things that fill their lives with joy and men are not exempt. If he happily starts talking about his passions and interests, that means he knows how to create happiness in his life and won’t be solely relying on you for that. A guy who shrugs the question off or makes it seem silly is clearly going to have a hard time communicating and opening up.
  9. Do you want kids? I don’t want children, so I’m not going to pursue a serious relationship with a guy who does. If having kids is important or a dealbreaker for you, it’s best to know where the guy stands from the outset. No point getting attached to him only to discover months or years into the relationship that you want very different things.
  10. Is monogamy for you? Some people don’t do monogamy and that’s quite alright. If that’s him and you’re looking for a guy who’s happy and content being with only you, then a second date is out of the question. Similarly, if you’re not into monogamy and he is, there’s no point in continuing to see him. Try to ask this question in a casual, non-judgmental way.
  11. How do you feel about (insert topic)? Discussing politics and ideologies is a good way to figure out whether you can build a serious relationship with a guy. Ask him about a subject that’s very important to you and listen to his opinions. If he doesn’t share the same stance and it’s an issue that you absolutely cannot budge on. a second date might not be on the cards.
A girl preoccupied with living her best life even when it's uncomfortable to do so. She spends a lot of time with her thoughts. She hopes you enjoy reading the results of those thoughts.