10 Easy Ways To Avoid Super-Awkward Online Dating Conversations

Dating online is hard as it is. Here's how to make things a little less painful.

Last updated on May 28, 2024

Key to avoiding awkward online dating conversations Martin Dimitrov, glegorly | Canva

Talking to guys online is so nerve-wracking! Often, you don't know what to say, or you're afraid that you'll say all the wrong things. You aren't dating yet, and probably aren't completely comfortable around each other. While it can be intimidating, the more you put yourself out there and talk to guys, the easier it will be. Honestly, there aren't any hard and fast rules on how to start a conversation online, but here are ten ways you can turn the charm on and keep the conversation flowing.


Here are 10 easy ways to avoid super-awkward online dating conversations:

1. Make sure you read his entire dating profile before you meet.

This might sound obvious, but read his profile and get a sense of who he is as a person. Scan it to uncover aspects of his likes, personality, or sense of humor, so you can have something to bring up if you're ever caught in a conversation "black hole" and don't know what to say. Awkward moment of silence? What about his favorite movie that stars your favorite actor? Or maybe that band he's been into lately that you've liked since high school? Take the time to use a profile to give your conversation fuel


RELATED: If You Have These 3 Skills, You'll Rule The Online Dating World

2. Know what typically appeals to men like him. 

Men like women because they're, well, the complete opposite of them. They like that you're feminine, fun, confident and you like yourself. You should have your own profile written in a way that appeals to men, instead of broadcasting your "want list." So talk less about what you want and more about what would interest him about you. If you want a good conversation with a guy, make sure that your profile and pics demonstrate you're worth talking to in the first place.

3. Pay attention to what he gets excited about.

Maybe he's a big fan of hiking up mountains, or he has a child. If he mentions that something means to world to him, talk with him about it. Why? Because people like to talk about themselves. They like to talk about what has meaning in their life. When you, an outsider, get this, you will make him feel special and understood.


4. Make him feel valued.

Whether it is your job, dating, or family life, we all like to feel valued, important, and appreciated in someone's life. So if you demonstrate this in your conversation you will make him feel good, and stand out from the crowd.

RELATED: 5 Weirdly Effective Ways To Get A Guy's Attention Online, As Confirmed By Men

5. Share something interesting about yourself.

It is really hard to talk to someone you don’t know. So be open and share a thought, a story, or an opinion about yourself. Show him there is a real woman behind the email with personality and character.

6. Don't be afraid to mess with him a bit.

Go ahead and play with him a little — tell him how awful the shirt is in picture two and how it’s lucky he is cute so he might just get away with it. Don’t be afraid to have a little fun with your conversation.


7. Keep things light and casual.

Talk about everyday stuff or little things that let him know he's a welcome distraction. Did your dog steal the neighbor’s clothing off the line that day? Did you have a hysterical joke that you're dying to share? Any news that might tickle him? Are you hiding in your room from guests so you can talk to him for a moment? Remember that not everything needs to be so serious all the time.

RELATED: 10 Signs Your Online Relationship Could Lead To Lasting Love

8. Make your conversation a back-and-forth interaction.

Ask a question and tell him something about your life. Give him a chance to say something back, too. Make sure that you're not hogging all the attention or forcing him to put in an obligatory 'k' while you're typing a novel about your day.

9. Don’t talk about past relationships.

Don’t talk about exes, how you're liking a dating site, what you hate, how afraid you are of getting hurt, or other topics that might swing the conversation in a sour direction. Saying that you liked his profile so you thought you would reach out to him and give it a try is a bit cliche. Instead, pick one topic that you got from his profile that interested you — and never, ever, compare him to your ex! 

@getnaturaljackson Stop talking about your ex with your current partners 🥴 It’s not a good look. Be in the present moment and enjoy the person you’re with, with no strings attached 🙅‍♂️ . . . #growthmindset #confidenceiskey #harnessyourpower #relationshipgoals #takecareofyourself #adviceformen #relationshipadvice #relationshipadviceformen #datinglife #datingtipsformen #loveadvice #menshealth #menshealth #menshealthtips ♬ Beat - beaty

10. Understand that there are no hard and fast rules.

What will work for one guy won’t work for another. My advice is to pick "relationship-ready" men. You can pick up on this by how their profile is written and the email responses they send. Again, always make sure the guy is stepping up and making the effort, and that you are reciprocating. If he has not asked for your number after 5-7 emails, it might just be best to let him go. One of the secrets to successful online dating is being clear on what you want in the first place, focusing on qualities you have to offer, and understanding that if you don’t change the common negative dominator in all your past experiences, you will get the same result. How to have a great conversation online with a guy is no different than talking to someone in public. Be you, be real, and have fun!

RELATED: 15 Brutally Harsh Things Guys Won't Tell You About Your Dating Profile

Lorna Poole is an international coach and professional speaker. She empowers women to love beyond fear, pain, and regret to attract the partner they truly deserve.