How To Text A Guy To Start A Conversation: Messages To Send Him To Get Him Talking


Like it or not, many if not most of our conversations with potential dates take place via text, at least at the beginning. That means it’s important to ensure that whatever you’re saying to him is engaging and likely to get you more than a one-word answer. While you should never be the one doing all the work when it comes to talking to a guy, here are some texts you can send him to start a conversation.

  1. Ask him questions that require thoughtful answers. Messaging him to simply say “what’s up?” might be cool when you’re months into a relationship, but when you’re first getting to know each other, this kind of text won’t get you much of a response (if he bothers to answer at all). If you want to start a conversation with this guy, bring up topics that require him to put together a few sentences or maybe even a paragraph of a response. Ask him something about a particular topic you know he’s knowledgeable on or even about something he experienced that day that you know will make a good story. That should get him talking.
  2. Tap into his interests. No one wants to talk about stuff they don’t care about, so if you want to strike up a conversation with a guy you like, the best way to do it is clearly to talk about things he’s actually interested in. While you shouldn’t have to pretend you care about the Playstation 5 or the latest football match, tapping into your shared hobbies or even something you’re interested in that you know he’s all about is a good way to inspire him to chat. He’ll be happy to have someone into the same things he’s into and he’ll likely be more willing to expand on the convo.
  3. Tell him something weird/crazy/funny that happened during your day. If you’ve got an amazing story about something that happened while you were at work or out and about that you know would make him laugh or shock him, tell him about it! There’s nothing better than being able to make a guy crack up, so if it’s funny, this is even better. Send him a text telling him the story – if he can tell you’re amped up over it, he might be more inspired to join in on the conversation.
  4. Bring up something he’s mentioned previously. If he recently mentioned that he wanted to go to California to see his mom or that he wondered what the new Japanese restaurant in town is like, bring that up when you’re texting him. Whether it’s in the context of just asking how far along his plans have gotten or even setting up a date by asking if the guy wants to check out their food with you, if he’s interested in you at all, he’s much more likely to be into the conversation and want to keep it going.
  5. Ask for his opinion/recommendations on something. Again, this is a no-brainer. If you want his recommendations on what book you should read next when you know he’s a huge reader or where to get a new pair of sneakers for the gym because you know the guy is big into his sportswear, ask him! He’ll be thrilled that you thought to send him a text and his ego will be stroked by you asking for his opinions.
  6. Flirt unabashedly with him. If ever there was a way to start a conversation with a guy via text, it’s this. Obviously you shouldn’t do this if you’re not at that stage in your relationship, but if you think he’d be into it, why not send a little flirty message? If he feels the same way about you, your phone will be buzzing in no time.
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