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! First and foremost, be honest. Your partner may have also done some of the things you did and you could have a new activity to revive together. 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. Make Things Fun. It can be difficult to have a serious conversation with your boyfriend. All of that said, don't feel pressured to talk 24/7, if you (or your partner) don't want to. Often, people will date the same type of partner over and over again. It means more things to do together and more things to talk … It’s an entertaining thing to talk about and you can both laugh at how silly you were when you were kids. It's time to ask some serious questions and find out if it's worth going ahead. What made you break up with your last girlfriend? Instead of avoiding a difficult discussion, it's almost always better to talk … But instead of finding out where your boyfriend wants to settle down, you can find out what type of vacation your boyfriend likes. In fact, I highly recommend having this talk. By learning why he broke up with his last girlfriend, you can figure out what the potential problems in your relationship will be. Of course two cannot … If you both like the same stuff, that’s always better. There's no point going into a serious relationship talk with your partner if you are going to hold things back. 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. As the female, you need to ask your boyfriend some serious questions about your relationship so as to know what to expect. Your past is always a fun topic. (We aren’t married.) Get talking about some of these things and you might learn things you never knew about your man. 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. 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. This one is similar to the “where would you live” question above. You can talk long term or short term, or, if it’s a new relationship, you can even just talk about what you’re going to do together next week. Ask these 10 relationship questions relatively early on to avoid heartache and missed opportunities. Serious Questions to Ask Your Boyfriend About Life, Future, and More. 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