Want To Know If He’s Worth It? Ask Him These 15 Questions

While you don’t want to lay on the heavy questions when you’re just getting to know a guy, you should try to find out if he’s date-worthy or not before you waste too much time. When you’re sizing him up across the bar/restaurant table, make sure you ask him these important questions to help you decide:

  1. What do you regret? Everyone has regrets and the type of regret he has can tell you a lot about him. The most important thing, however, is if he’s learned from the mistakes he’s made. This awareness is what’s important so that you know you’re dealing with someone who takes responsibility for his actions and improves himself.
  2. What do you want? This should apply to life and relationships. As much as you want to play it cool in the early days of dating someone, you deserve to know if he’s looking for a real relationship and not just a booty call.
  3. Are you a phone person? Some guys just aren’t into using the phone a lot to text, so it’s good to know upfront if you’re dealing with a guy like that. It will prevent you from wondering where he’s at when he doesn’t text. If he’s not a phone person, he should say that he makes contact with people regularly in other ways and most importantly, he likes seeing people in real life.
  4. What’s your biggest goal? Make sure you ask about short-term as well as long-term goals. The long-term goal will give you an idea of the big picture he wants for his life, but the short-term goal will show you what he’s dealing with right now. It tells you where he’s at, and that’s important for you to know if you’re going to keep dating him.
  5. What’s your family like? He doesn’t have to be on the best terms with his family, but he does need to care about them and make time for them. These relationships are important and if his family relations are riddled with drama, it’s a sign that something’s not right. He might be a drama magnet boyfriend!
  6. Why did your last relationship end? It’s not enough to know how long he’s been single. You need to know WHY he’s single. He might say that he and his GF went different ways, but get the details on that. He might be honest and tell you bad things he did, such as cheat on his partner, which is a huge sign that you can do better with someone else. If he trash-talks his ex, it’s a bad sign that he’s not a good guy or not completely over the breakup.
  7. What was your childhood like? You shouldn’t judge people based on their past, but it’s sadly true that we’re all influenced by what happened to us as children to some extent. If the guy had a really volatile, stressful childhood, there are definitely still issues he’s dealing with. The sooner you know about them, the better.
  8. What are your deal-breakers? You need to know what he won’t put up with in a relationship. Surprisingly, his answer might show you that he’s not right for you. For instance, a guy who says he won’t date a woman with a tattoo could seem really judgmental or boring to you. By asking about his deal-breakers, you can find out about his lifestyle (such as if he’s vegan and won’t date non-vegans) and relationship needs.
  9. What do you expect from a partner? This is important because everyone has different relationship expectations and you need to know you’re on the same page. He might want a partner who spends all her free time with him (clingy man alert!) or doesn’t expect him to call her often (nice way of saying he’s not going to make a lot of effort).
  10. What’s a regular day like for you? This might sound like it isn’t much, but you can find out a lot! Does he gym daily? Does he work? Does he spend time with his friends at the pub every single day? Does he eat out every day or like to cook healthy meals at home? Does he spend some time in nature or does he spend the majority of his waking hours stuck in front of a computer screen?
  11. What do you like to do on weekends? This gives you a good idea of the interests he pursues and how important his friends are to him, so you can see if your social lives work well together.
  12. What’s your biggest motivation? This shows you where he’s going in life and what the payoff for all his hard work is. Is it success, status, money or happiness?
  13. What makes you laugh? You want to be with a guy who has the same sense of humor as you do. Humor can also reveal aspects of his personality. If he likes to laugh at the pranks he and his friends pull on people, he might be a bit childish. On the other hand, if he likes witty humor, it could point to intelligence.
  14. How do you show your love? Everyone shows their love in their own way, but you want to know what you’re dealing with in a future boyfriend. For instance, does he shower his partner with lots of gifts and surprises? Although that’s sweet, maybe he’s trying too hard to sound like Mr. Perfect. You want a guy who shows his love by having quality time with those he loves and supporting them. And, of course, a guy who wrinkles his nose or scoffs at a question about love isn’t the kind of mature guy you want to be around.
  15. Do you think men and women can be friends? This is the age-old debate, but can be useful to ask a potential boyfriend. If he thinks men and women can’t be friends, then you’re going to be wary of any women he talks about in your relationship. On the other hand, a man who says women and men can be platonic and has a lot of close female friends, has healthy relationships with other women which will make him a better boyfriend.
Giulia Simolo is a writer from Johannesburg, South Africa with a degree in English Language and Literature. She has been working as a journalist for more than a decade, writing for sites including AskMen, Native Interiors, and Live Eco. You can find out more about her on Facebook and LinkedIn, or follow her on Twitter @GiuliaSimolo.