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Starting a Conversation with a Guy without Being Intimidated

You find someone who interests you, and you can’t wait to talk to them, there’s just one issue: you don’t know how to start a conversation with the guy you like.    

How to start a conversation with a guy

Whether you met someone in a bar, at work, or online, the first conversations with someone you have interest in is integral. 


Especially in dating culture today, many people lose interest quickly, especially online. In my opinion, the best way to communicate properly, to learn people’s intentions, body language etc, is through meeting and talking in person.


 When that isn’t possible there’s some ways to make sure your conversation doesn’t fall flat.  


Starting a conversation with a guy you like virtually is really hard. Whether the conversation is starting over text, over the phone, on video chat, or just online it’s different than in person! 


Especially with COVID, relationships seem to have more and more aspects of long-distance, and you never know when you aren’t going to be able to see someone. 


I understand these problems so much because I began a relationship myself over COVID and my only form of communication was virtual. Hopefully I can help someone else like me out, who hated technology as a form of communication and shunned it for years.


Below I have some ways to start a conversation with a guy you like over the phone, whether it be text, phone call, messaging, or video chat. 


how to start a conversation with a guy online

How to start a conversation with a guy you like over text


Getting to know another person is nerve wracking and texting makes the process even more difficult. I’ve spent so much time obsessing over every little text I have sent to a guy, and so have all my friends. 


Will this text be interesting enough? Will they still like me? And other thoughts like these are going through my head. Here are some ways to get around that nervousness


One tip is to get creative! Ask questions to learn about them, share fun facts, your interests, hobbies, things you do on a regular basis. You want to know if this guy is going to be compatible with you, so start to learn his interests. You’ll quickly be able to learn his communication style when you keep texting. 


Some starters: 


  • Be sure to ask open ended questions, a yes or no question doesn’t stimulate conversations and leads to someone having a easy way out of a conversation with limited effort. 
  • Give them a compliment! 
  • Find a shared interest. 
  • Ask for recommendations on shows/food

120 Questions to ask a guy over text

How to start a conversation with a guy on the phone


While texting can be difficult, there are other ways to talk virtually! While a lot of people prefer to text rather than talk on the phone, so many people I know (myself included) will only talk on the phone, and absolutely hate trying to text to communicate.

Texting and social media has allowed for the personal connection to sometimes be lost in dating and communication. 


When I’m dating I much prefer to talk on the phone rather than text because I can actually understand tone, and texting makes me super anxious when I don’t know someone well (even people I do know well!!).

Talking on the phone is a good middle ground between texting, video chatting, and seeing each other in person.


Similarly with texting, a lot of the topics/conversation starters for a conversation on the phone center around the basics of getting to know someone. 


Another positive is flirting is so much easier when you hear the other person’s voice over texting. Tell them about your day, sprinkle in how you are excited to see them, your next date, hearing about their day.


All of the above are so helpful to stop a conversation from falling flat. You can even play games over the phone. Literally the options are endless to get to know someone, even on the phone.  


how to start a conversation with a guy over text

How to start conversation with a guy online


Especially with COVID, our ways of communication have changed drastically. As someone who was taking classes at points during the time of COVID, zoom became my best and worst friend. 


It was great for my relationship and being able to see each other, but obviously it became a bit frustrating. With our technology now, being away from someone is a bit easier to get through with the use of Facetime, Zoom, and other video chatting software. 


There are so many great programs and options for people who are long-distance now, and I can’t wait to share some of my favorite things to do, talk about with a guy (girl/person) who you like. 


Looking at facetime and other formats like zoom allow for a lot more personal connection. If you haven’t met before you can show them around your home, your town, your favorite places. 

Rather than just starting with a specific topic, you can suggest a virtual date night! Netflix party is a great way to watch a movie online with your crush while you are still able to see them and message throughout it to each other.


You can have a game night and play some online games, and even spice it up a bit with a wine or drink night together.

Some of my favorite nights when I wasn’t able to be with my boyfriend was having virtual wine and movie nights on zoom. 


If you aren’t having a date, and its just a quick call, you can even do something like the Wordle together, something that brings you both together in a way outside of texting. 


how to start a conversation

How to start a flirty conversation with a guy

While getting to know them, you also want them to know that they are your crush. You have to be more vulnerable and flirt with them! You can make most conversations flirty if you put some effort in. 


  • Give them a compliment about how they looked the other day! Stay away from the “sexy” “hot” words and make a point to be genuine. 
  • Find a common interest (tv show, music) and start up a conversation about it
  • Use Memes!
    • Nowadays so many people use memes as a form of communication, and I can’t lie.. I do too! The same thing goes with TikTok, you see something interesting which makes you think about them? Send it and it begins the conversation
  • Tell them you are thinking about them
  • Ask them about their next plans to see you. 
  • Ask their intentions
    • This one is a big scarier and depends on the situation. You don’t want to ask the question too early and scare them off, but you don’t want to get into a situation where you guys aren’t looking for the same thing. Be honest and tell them what you’re looking for before feelings get hurt. 
  • If you are seeing them soon, tell them you are excited to see them, or can’t wait for your date/hangout/meetup
  • Mention things you could do together

75 Flirty texts to make him want you


Conclusion: how to start a conversation with a guy


While initially you may think communicating online, texting, or otherwise on the phone with a guy you like may be impossible; you really have such incredibly options.

Talking virtually can allow you to get to know someone better if you are worried about meeting in person, you don’t like particularly close, or you are just apart and starting to date. 


My biggest advice for talking to someone you like is just dive into it. Send the text, dial the number, don’t play games and be genuine. It is the best way to get to know someone, especially online. 


Happy dating!

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