How to Start a Conversation with a Guy Online

One of the scariest things a guy can do is approach an attractive girl and start a conversation with her. So many thoughts run through our minds. What if I’m rejected? How do I start the conversation? Hopefully, the conversation goes well, and you get her number.

Approaching a woman is stressful enough for men. It’s downright terrifying for women. Most women have never made the first move with a man in real life, let alone online. So, women have the same fears of rejection as men.

But women, more than men, believe that if they make the first move and message a guy from a dating app, he wouldn’t be interested. Women frequently need to learn how to start a conversation with a guy online once a message has been sent.

In this article, I decided to help women out by showing you how you can start a conversation with a guy online. By the end of this article, you will know how to create and keep the conversation going, pique a guy’s interest in you and look at some examples of conversation starters.

How Do You Start a Conversation with a Guy Online?

You can take several approaches to start a conversation with a guy online. In today’s modern online dating era, most people find dates and meet new people via online dating apps or dating sites.

Examine the guy’s dating profile

Specifically the “about me” or “Bio” sections. What you want to do is look for something interesting about him you can use to start a conversation. Maybe he loves comedy sitcoms and mentions that his favorite show is “Big Bang Theory” or “Blackish.” You also love those shows. You could start the conversation by asking about a character from the show. Or by asking him what he thought about the last episode.

Ask him what he thinks about the dating site or app..etc.

I like asking people what they think of a site if they are new to online dating. You can usually tell someone is new to internet dating by their profile – there is minimal information about them in their “about me” section, and there may only be 1 or 2 pictures posted. When you lack experience dating over the internet, you don’t leave conversation breadcrumbs in your profile you can use to converse. This question can be an easy ice breaker that can lead to more light personal questions.

Start a conversation by asking, “What’s the last… i.e., concert, movie, or vacation you were on?”

This is another good question to ask a guy if you have read over his profile and need help finding something interesting to ask. You also stand out to him because you get him reminiscing about the last movie, concert, or vacation he was on or experienced. Most of us enjoy going down memory lane.

Pick something from his profile and make fun of him for it.

This is an excellent approach if you have a sense of humor and want to attract a guy who enjoys laughing. Just be cautious; a joke or teasing via texting doesn’t always go over so well as the same pun told in person. Whenever I’m joking with someone online, I use “LOL” or say, “I’m just joking,” so there’s no confusion.

Ask him a personal question…Just keep it light and fun.

How to Keep the Conversation Going?

Now you know how to approach and open a conversation with a guy online. Let’s look at ways to keep the conversation going.

You can keep conversations going by asking the guy at the other end of the keyboard questions. Only some questions are created equal; you don’t want to ask a question that can be answered with a simple yes or no.

Ask your crush open-ended questions. These questions can’t be answered with a simple yes or no but require the respondent to elaborate to answer the question.

For instance, you message a guy on a dating site that’s into fitness. In your first message, you ask him how long he has been into working out. After his response, an excellent open-ended question could be, “What made you get into working out or fitness?”

This question requires more than a simple yes or no answer. The guy has to explain his reasoning thoroughly. Elaborated answers extend conversations, and the more you learn about a guy in a conversation – the more information you have to steer the conversation.

Note: If you want more tips to keep a conversation going with a guy, check out “How to Keep the Conversation Going on a First Date With a Guy” for more information on extending a conversation with a guy.

how to start a conversation with a guy online - image of a woman at her computer

How to Keep Him Wanting More?

You have learned how to keep the conversation going, but you want to keep him wanting more. Now let’s focus on getting him interested.

You keep a man wanting more by stimulating him mentally. You build interest in men by asking thought-provoking questions. Again, these questions are open-ended. You’re not looking for yes and no responses. 

We all love talking about ourselves. It is how we all connect and build bonds.

Taking the last example from above, you ask a guy the question, “What made you get into working out?”. This question stimulates him mentally because he is required to travel down memory lane to a time when he isn’t healthy.

Maybe he was 100 pounds heavier. And in answering your question, he shares his weight-loss journey with you. This may be something he has never shared before and is proud of.

By asking this question and allowing him to talk about himself, he will feel a connection that will keep him wanting more from you.

The Takeaway

For many women, starting a conversation with a guy online is challenging. What do you say? How do you start the conversation?

In this post, I shared 5 ways you can start a conversation with a man online by:

  • Scanning his profile for something interesting to talk about
  • Ask him for his thoughts on the dating app.
  • Start a conversation by asking, “What’s the last…ie.
  • Pick something from his profile and make fun of him for it.
  • Ask him a personal question.

Now that you know how to start a conversation with a guy online, it’s time to go to your favorite dating app and talk with men.