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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. By learning why he broke up with his last girlfriend, you can figure out what the potential problems in your relationship will be. Ask these 10 relationship questions relatively early on to avoid heartache and missed opportunities. First and foremost, be honest. Make Things Fun. (We aren’t married.) 21. If you’re looking for a more serious conversation to have with your boyfriend, try talking about your future together. 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? In fact, many couples nowadays are long-distance and the bulk of their communication happens over text. If you both like the same stuff, that’s always better. 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. It's time to ask some serious questions and find out if it's worth going ahead. 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. It can be difficult to have a serious conversation with your boyfriend. Your partner may have also done some of the things you did and you could have a new activity to revive together. 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. What made you break up with your last girlfriend? Your past is always a fun topic. There's no point going into a serious relationship talk with your partner if you are going to hold things back. But the healthiest and most fulfilling relationships involve individuals who are emotionally open with each other, and honest about who they are and what they want. As the female, you need to ask your boyfriend some serious questions about your relationship so as to know what to expect. Get talking about some of these things and you might learn things you never knew about your man. It’s an entertaining thing to talk about and you can both laugh at how silly you were when you were kids. Of course two cannot … Serious Questions to Ask Your Boyfriend About Life, Future, and More. 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. 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. In fact, I highly recommend having this talk. This one is similar to the “where would you live” question above. 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. 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. 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. 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