Are there certain uncomfortable questions that are actually important to ask in a relationship?

I think asking awkward questions is actually a fun way to break the ice and see how comfortable a guy is with open conversations. Sometimes, the best responses come when people are caught off guard! That said, timing is everything—some questions are better for later stages of dating when there's already some trust. But overall, I think it’s great to ask bold questions because they often lead to more honest and meaningful conversations.

Awkward questions can actually be a great way to get to know someone on a deeper level. The key is asking them in a playful, curious, or lighthearted way so they don’t feel like an interrogation. Some of the most revealing questions include topics like past relationships, biggest insecurities, or even thoughts on commitment and marriage. These might feel uncomfortable at first, but they can lead to really honest discussions. I found a great article that lists some of the best awkward questions to ask a guy and explains how to approach them awkward questions to ask a guy https://apericor.com/dating/relationship-advice/awkward-questions-for-couples. It talks about why these questions matter and how they can actually help strengthen a relationship rather than make things awkward. Have you ever asked a guy a really uncomfortable question that ended up leading to a deeper connection rather than making things weird?