How To Start A Conversation With Your Boyfriend

Updated October 5, 2022 by BetterHelp Editorial Team

The first weeks and months of a budding relationship are often filled with hours-long conversations and exciting late-night phone calls. You both can’t wait to talk with each other as your relationship grows. You hate when your conversations are over and can’t wait for the next opportunity. But after those early days, the talk might not flow as easily. The newness has worn off and it’s time to find some ways to jumpstart the conversation.

Struggles with Communication Are Normal

Maybe your conversations were great in the beginning, or maybe it’s always been a struggle. Communication issues are normal but can also be a red flag of a relationship in trouble. It doesn’t mean you need to call it quits. There’s much you can do.

Effective communication is important for your relationship so you can truly know your partner and resolve differences. Being able to communicate will help you move past problems that could have otherwise tripped up your relationship.

Find Out What He Likes

Better Communication Skills Can Strengthen Your Relationship

One of the best ways to connect with a person is to focus on their interests. Lots of topics of conversation can come from merely finding out what your boyfriend likes and going from there. If you’re in a new relationship and don’t know the answers to questions, like what he does in his spare time, what his hobbies are, what his favorite place is, who is his role model, who are his best friends, and what his dream job is, ask!

Find out what kind of books he reads, movies and television shows he watches, and what kinds of sports he likes to play or watch. Is he an intellectual type? Does he talk about politics or law? Is he interested in current events? Now is the time to figure out what you two have in common and find some common ground.

A fun method is to play twenty questions, relationship style. There are lots of good questions you can find online, print out, cut into strips, and pop in a fishbowl. Questions like “If you won the lottery tomorrow, what would be the first thing you would do with the money?” Or, “If you could have lunch with anyone in the world, living or dead, who would you want to meet?”

Be sure to inquire about his past. What was his favorite movie in childhood? Maybe you two could watch it again. Did he have a favorite album growing up? Find out and play it in the car while you are headed out on a date. Look at old family photo albums and ask about the people in the pictures. However, refrain from discussing past relationships as that may only make him feel awkward.

As long as you are genuinely interested in getting to know your boyfriend, asking targeted questions about his interests and his past will help get the conversation going and build connections. Relationship experts often encourage the use of conversation starter questions.

However, it’s also a good idea to ask more open-ended questions as well. If you focus on asking specifically yes or no questions, then you may have a hard time getting the conversation going. Open-ended questions push your boyfriend to explain their responses which gives you more things to talk about and keep the conversation going.

Tell Him What You Like

If you’re having trouble getting him to open up, maybe it is time to talk about yourself. Tell him what you like to do when you’re not working or with him, what you want to do this weekend, what you wish you could do, or even what you want to do in the future.

In fact, future plans are a great conversation starter that can open him up about what he wants to do in the future. Furthermore discussing your past is another great way to start conversations. Therefore, tell him what your childhood was like, what your family is like, your favorite books and movies, or what games you like to play.

If you are still new to the relationship, it may not be a good time to talk about how you want to get married and have kids, so be mindful of that! If you don’t know where to start, use some of the conversation starters we talked about above, but in reverse. Tell him what makes you the happiest, the strangest movie you’ve ever watched, and the craziest thing you want to try someday. Just make sure you bring the conversation back around to him at some point.

Play a Game

If twenty questions feel too awkward, play a different kind of game. Chess, Checkers, Scrabble, Sorry, and other types of board/card games are fun, yet intimate and might be the perfect icebreaker that leads to conversation topics without the talk being “forced.”

When you’re feeling a little braver, try a game like “no words” in which you each ask yes-and-no questions over drinks. For example, you might ask, “Were you nervous on our very first date?” You answer by drinking. One sip means “yes,” while two sips mean “no.” You can ask thought-provoking questions or fun questions, just keep the conversation moving.

Two truths and one lie is another game you can play with your boyfriend as a way to start a conversation. With this game, you take turns telling each other two fun things that are true and one that is not. The other person is responsible for deciding which is the untruth. 

Talk about Nothing

Sometimes it is okay to sit and enjoy the silence. While some people find it uncomfortable just to have quiet companionship, it is a great way just to enjoy each other’s company. Once you move past the stage of getting to know each other, sometimes it can be forced to keep a conversation going at all times. If this is the stage that you’re in, don’t feel bad about it.

However, if this makes you uncomfortable, or you’re still working on building the relationship, don’t be afraid to talk about nothing. Or anything. Think of something you heard on the television or some gossip you read in a magazine. If all else fails, talk about the weather.

If you’re truly struggling with fun conversations, it could be for many deeper reasons. Social anxiety could make you uncomfortable talking, even though you really want to. Or it could be that you lack self-confidence which makes it hard to decide what to talk about.

Try some conversation starters

Better Communication Skills Can Strengthen Your Relationship

If you’re struggling to have a good conversation, you may benefit from trying to use conversation starters in your relationship. They provide you with new things to talk about and open the door for further conversation. They could be fun questions or thought-provoking ones. Even if you’ve been in a long-term relationship and feel like your partner is your best friend, you can learn more about each other.

Here are some conversation starters to get you thinking (and talking):

  • What would you like to be remembered for?
  • What’s your favorite thing that we’ve done together?
  • Do you think you are a confident person? Why or why not?
  • What was your best and worst childhood memory?
  • What would your worst day or perfect day look like?
  • What’s your favorite vacation to date?
  • How would you describe your best and worst moments in our relationship?
  • What’s the best way for someone to improve themselves?
  • What are the five things that made you who you are now?
  • What’s your favorite way to spend a Saturday morning?
  • What makes you feel appreciated in our relationship?

You can also try to come up with some conversation starters on your own. You and your partner could write out random things to talk about on slips of paper and draw them out of a hat. This combines conversation starters with a game you can play together.

If your conversations are a struggle in your relationship, individual, couples, or family therapy can help you learn how to improve your communication skills. Doing so will help your relationship. BetterHelp has online counselors that can work with you on an individual level or with you and your boyfriend together. You can read some reviews of our BetterHelp counselors below.

Counselor Reviews

“Erin really helps me set goals for communication, and it’s really crazy how much it’s improved the communication in my marriage. She also asks me every week what I’d like to work on, so it’s just really great to be able to decide and then to put it into action. Without her, I wouldn’t even know where to start.”

“Mark is an amazing therapist. He listens so well and has such valuable insight on male and female perspectives and issues while also not passing judgment. I have only just begun, but he has already given me so many great takeaways to improve my relationships and situations. I am filled with gratitude, and I would highly recommend him to anyone!!”

Signs that you may want to talk to a relationship expert

If you’ve been in a long-term relationship and are struggling to have a conversation together, it may help to get relationship advice from a relationship coach. This could include a marriage and family therapist or a dating expert. There could be obstacles in your relationship that are causing the conversation to be difficult, to the point that a simple list of conversation topics or conversation starters won’t help.

Look for red flags such as:

  • Beginning to withdraw from one another
  • Losing interest in one another
  • Arguing more than you talk
  • They never move past surface-level conversation topics

Even if it’s as simple as a gut feeling that you have instead of major red flags, speaking with a relationship expert like a dating expert or marriage and family therapist may be helpful.

If you’re having difficulty talking with a new boyfriend or girlfriend, it could be one of the red flags that you may not be a great fit. While it’s normal to benefit from the use of conversation starters as you get to know each other, if conversation doesn’t eventually begin to flow on its own, it might not be worth forcing. Take a minute to look at your relationship and see if there are other red flags that it might be better to end the relationship before it hits long term status.


Communication in your relationship can always improve. Use the tips above like the conversation starters to spark conversation with your boyfriend. You may find even with silly fun questions, that he becomes not only your romantic partner but your best friend as well. With the right tools, you can strengthen your relationship.

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