How To Keep A Conversation Going With A Guy

You’re talking to a new guy and things are going pretty well. You have a lot in common, the chemistry is there, and you think there might be a chance of something good happening here. However, you can’t help but notice that sometimes your chats start to drag a bit. You still want to talk to him but you don’t want to force things. Here’s how to keep a conversation going with a guy without it being weird or awkward. Don’t worry, you’ve got this.

How to keep a conversation going with a guy you’re talking to?

  1. Be confident. There’s nothing men love more than a woman who’s self-assured and confident in her own skin. Go into your chats knowing that you have a lot to offer and he should pick up on that. “Be bold and unafraid when you talk to him,” advises sex therapist Aliyah Moore, Ph.D. “Good men respond well to confidence; if they’re threatened by it, then they aren’t worth your time. I’m not saying you should sound full of yourself, but try your best not to be shy.”
  2. Show genuine curiosity. He’s not going to want to keep talking to you if he doesn’t think you’re interested in what he has to say. Sure, you’re not going to care about every aspect of his life, but there should be something about him/his life that intrigues you. Otherwise, why would you even be into him? Ask him about parts of his life that you find fascinating and he’ll have plenty to say.
  3. Drop the ulterior motives. If you’re constantly trying to think one step ahead during your chats, you’re doing it wrong. You should enjoy talking to him for the sake of it, not because you’re hoping it’ll lead to something else. Stay in the moment and your organic conversation will go much better.
  4. Ask open-ended questions. This is one of the easiest ways to keep a conversation going with a guy. Asking him questions that require a simple yes or no answer is a no-no. It gives him nothing to go on. Instead, discuss topics that require some amount of elaboration. Even better if it’s something you both can add your input on.
  5. Send memes. It sounds silly, but if you want to keep a conversation going with a guy, this is a great option. “If you see something cool on one of your apps, share it. Not only does this give you a chance to laugh at something together or discover shared interests, but it makes him feel more secure about sharing things with you too,” Moore suggests.
  6. Be willing to open up about yourself and your own life. Conversation is a two-way street. You can’t expect him to share things about himself and his life when you’re not willing to do the same in return. Sure, you don’t want to tell him your deepest, darkest secrets (at least not right away), but if you want vulnerability, you have to give it back.
  7. Suggest a different mode of communication. If the convo is lagging via text, ask him to FaceTime. If you’re doing video chat and it’s getting a bit blah, plan to hang out in person. It could just be that things aren’t flowing as well because of the medium you’re using to communicate. It’s worth a try!

What to do if you’re not getting much back

  1. Offer to continue the conversation another time. Maybe it’s not that he doesn’t want to chat, he’s just busy and has a lot going on. If that’s the case, offer him an out by telling him you can message him later. Or, better yet, invite him to reach out to you when he gets a break. He’ll appreciate you taking the pressure off and giving him the space he needs.
  2. End the conversation for now. Just because a conversation isn’t flowing doesn’t mean you should never talk again. In fact, sometimes you’ve said all you need to say right now. In that case, rather than trying to keep taking, take a break. Know when things have run their course for the moment and let him know you’ll catch him later. Chances are, you’ll have more to say the next time.
  3. Don’t immediately write him off. While things might seem a little off to you, it could be no big deal. Not all relationships are smooth sailing right from the beginning. As Moore suggests, “Don’t give up right away if a few of your conversations are duds. Some
    people really just have nothing to say about a certain topic, and that’s okay. Try talking about different things to see if it’s the conversation that’s the problem or if it’s just him.”

When to throw in the towel/stop trying

No one wants to feel like they’re wasting their time and energy on someone who just isn’t feeling it. There’s no sense racking your brain on how to keep a conversation going with a guy when he doesn’t really want it to continue. There are a few ways to approach the situation, but in general, it’s important to do some self-reflection and put some space between you. Ultimately, you may realize it’s better to move on.

“If you really think you have tried everything and are not getting much back, maybe you need to give them some space. Ask yourself if you’re being overbearing or too demanding. What are the expectations around having conversations and engaging? Perhaps this guy is more into action like they would rather go hiking with you rather than talk over the phone,” says registered counselor and couples therapist Aditi Jasra.

“Use your intuition to guide you on whether the other person is really disinterested or unresponsive to your efforts to connect or whether they are simply busy or have other things demanding their attention. Conversations and relationships cannot be forced. If it seems like too much work, perhaps it is time for you to let it go.”

Bolde has been a source of dating and relationship advice for single women around the world since 2014. We combine scientific data, experiential wisdom, and personal anecdotes to provide help and encouragement to those frustrated by the journey to find love. Follow us on Instagram @bolde_media or on Facebook @BoldeMedia