I’ve been seeing this guy for a while, and things are going well, but I feel like there’s still a lot I don’t know about him. I want to ask him some deeper or even awkward questions to really understand him better, but I’m not sure where to start. What are some awkward questions to ask a guy that won’t scare him off or make things too uncomfortable? Has anyone had experience with this, and how did it go? Any advice would be appreciated!
That’s a really good point! Asking awkward or deeper questions can definitely feel tricky, but when done right, it can lead to some great conversations. One approach that has worked for me is to introduce the questions in a casual, non-pressuring way. Guys can sometimes be less open about certain topics, so it’s important to make them feel comfortable first. You could try asking something like, "What’s something you think people misunderstand about you?" It’s a bit of an awkward question, but it can really lead to deeper insights into how he sees himself and how others view him. Another question might be, "What’s the hardest thing you’ve ever had to do?" It may feel like an uncomfortable topic, but it’s a great way to learn about his resilience and experiences without feeling too invasive.
If you’re looking for more ideas, you should check out this site: https://apericor.com/dating/relationship-advice/awkward-questions-for-couples. They have a list of awkward questions to ask a guy that can help guide your conversations to a deeper level. The key is to ask questions that show you’re genuinely interested in knowing more about him without making it feel like an interrogation. For example, you could say something like, "I know this is kind of random, but what’s something you’re afraid to admit to most people?" This can spark a thoughtful conversation, but it’s important to be ready to share something personal about yourself, too, so it doesn’t feel one-sided. Awkward questions, when asked with the right intentions, can actually bring you closer together and help create a stronger emotional bond.
