It doesn’t have to be about relationships or your sexual past, just easy things like how you played soccer in high school, or were the president of the chess club. There's no point going into a serious relationship talk with your partner if you are going to hold things back. Your partner may have also done some of the things you did and you could have a new activity to revive together. If you’re looking for a more serious conversation to have with your boyfriend, try talking about your future together. As much as I love asking my man some serious questions to find out what he's really thinking, a long list of deep questioning might feel like a bit straining, so I definitely recommend mixing up the serious questions with some fun ones to keep things light and keep the conversation moving! 30 Serious Questions to Ask Your Boyfriend 1. Your past is always a fun topic. In fact, many couples nowadays are long-distance and the bulk of their communication happens over text. Of course two cannot … What made you break up with your last girlfriend? When you are with them for more than a year or so, you will reach a point where you run out of stories to share, topics to talk about. Serious Questions to Ask Your Boyfriend About Life, Future, and More. In fact, I highly recommend having this talk. Often, people will date the same type of partner over and over again. (We aren’t married.) It’s an entertaining thing to talk about and you can both laugh at how silly you were when you were kids. If you both like the same stuff, that’s always better. You don’t have to get all of this off of your chest on the first date (frankly, no one wants that), but we suggest you avoid big problems down the road by discussing the following expectations before you get too serious with your partner. It's time to ask some serious questions and find out if it's worth going ahead. This one is similar to the “where would you live” question above. So, it has been awhile that you two are dating, but you want to know whether or not he is ready to take it to the next level? As time flies and your casual fling turns into a serious relationship, you finally decide to settle down and naturally run out of things to talk with your partner. All of that said, don't feel pressured to talk 24/7, if you (or your partner) don't want to. By “serious” things I mean long-term financial planning, whether he wants kids, his plans related to school and career, what would happen if one of us dies. Instead of avoiding a difficult discussion, it's almost always better to talk … As the female, you need to ask your boyfriend some serious questions about your relationship so as to know what to expect. Make Things Fun. Get talking about some of these things and you might learn things you never knew about your man. First and foremost, be honest. Ask these 10 relationship questions relatively early on to avoid heartache and missed opportunities. 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