Online Dating Tips: Conversation Starters

online dating tips conversation starters

Online Dating Tips: Conversation Starters Guaranteed to Pique His Interest

When it comes to online dating tips conversation starters, things can get very challenging and confusing. You see a great guy’s profile online or on an app.  The anxiety sets in: What if you have nothing to say?  How much is too much?   How do you engage a guy’s interest when you are competing with so very many other women?  In short, how do you not fumble the ball?

We are going to answer these questions and more in this blog.  First, you’ll learn messaging tips that make him beg to meet you, and then we will explore the best tips for phone and in-person conversation starters.

Online Dating Tips Conversation Starters:  Must-Have Initial Messaging Tips

For an initial message reaching out to a new intriguing match- share a specific experience you enjoyed related to an activity he mentions in his profile and add a question about it. For example, if he mentions Chaco Canyon, you might write, I love Chaco Canyon!  I got a very cool piece of Anasazi pottery from the Heritage Center that I keep in my office to remember that sunset.  Did you get go on that crazy pink jeep tour?

Another way to go, is to give him a sincere compliment. Something like, I just started running myself and noticed you did half of the NYC marathon. Not shabby!

 Online Dating Tips Conversation Starters:  5 Messaging Tips for after he’s responded to your initial message

  1. Bond by using his name if you have it and flirt by throwing in a bit of a challenge. Using his name is another awesome way to create a feeling of connection between you.  If he’s into baseball, something like, Well, Jason, what about a Red Sox-Cubs World Series? How cool would that be? This kind of flirting, coupled with your Diamond Self photo, is a one-two KO punch that is TOTALLY IRRESISTIBLE.
  2. Be upbeat and fun.For example, you could say, I just had a breakthrough in my lasagna recipe! One taste and you’ll be hooked (fair warning) 
  3. Be honest but no confessionals or TMI. For example, don’t want to message him about how you drank all last night and are sick at work now.  Be real, but don’t start out being overly personal.
  4. Make your messages about the same length as his. This is a fantastic and subtle way to bond. It will feel like you are having a balanced conversation and are on the same page.
  5. Be careful with spelling and grammar. Since all he has to go on are these messages, grammar at this point will affect the way he sees you. So don’t come across as sloppy or uneducated.

Online Dating Tips Conversation Starters: Overview of a Great Beginning

Ideally you want about 3-4 fun flirty messages on the app, 2-6 text exchanges, two phone calls and then to meet for coffee.  Don’t get stuck in a fantasy messaging relationship with the “perfect” guy whom you never talk to or meet try to hasten texting and actual phone contact.  Even though you may feel intimidated about talking to him, it will give you so much more info about your match– so that you don’t waste time.  You can feel a guy’s energy, his mood, and whether he is a good conversational match for you.

We want to be weeding out the Definitely Unworkable Dudes (DUDs), and a phone call is a very efficient way to do that!  In fact, in our coaching program we have found that what we call Seriously Terrific, Utterly Devoted Dudes (STUDs) will often call in the beginning without the woman asking to talk.  They are more successful and don’t want to waste time, so they are more interested and willing to connect via phone.

A guy’s availability for talking with you is very telling!  On the other hand, if he doesn’t meet with you after two or three weeks after matching on a site, or a week or so after an app match, move on.

Online Dating Tips Conversation Starters:  Initial Phone and In-Person Conversations

Your first contact with someone you’ve met online can be awkward, especially if you are used to texting as your preferred communication mode. But here are some easy ways to make sure you put your best foot forward and bond with a guy:

  • Smile and give the person your full attention (even on the phone, this will come across!).
  • Imagine you are meeting an old best friend and give the guy a warm hello as if he is someone who is in your inner circle.
  • Ask general, casual, open-ended questions like How did your day go? Where did you grow up? Do you enjoy living here? How did you get interested in X? What drew you to my profile?
  • Ask questions about the interest he mentioned in his profile.
  • Have topics ready to discuss around movies or TV shows, books, and news that you both may find interesting (nothing political or heavy).
  • Prepare your answers to the questions, What’s new? What have you been up to?
  • Share what you are enjoying, i.e., something like, I’m having a fantastic day playing hooky at the beach!  What about you?
  • Avoid discussing old boyfriends or relationships (the number one conversation killer on a first date); talking about marriage, kids, or sex; or discussing debt or health problems.

If you are meeting in person, make yourself as beautiful as your photo and dress down or up so you fit in at the meeting place.

Online Dating Tips Conversation Starters: Final Thoughts

If there was any connection at all, at the end tell the guy how much you enjoyed talking with him.  And that you would like to continue it sometime. In your journal, make a note to ask him about the topic you were discussing in your next conversation. If you don’t feel much chemistry but he seems like a good guy, remember that you are still going to try a second date.  Be sure to read my post on bringing out chemistry with a good guy.

Remember, safety comes first whenever you’re meeting someone in person. Google the guy and check him out on Arrange to meet in a public place. Then, tell a friend where and with whom you are meeting. And be sure to take your phone.

If you follow these Online Dating Tips Conversation Starters you will be well on your way to having a great connection with a guy who could be the one. For more in-depth dating advice be sure to pick up a copy of my newly revised best-seller, Love in 90 Days. And if you’re struggling with meeting the right One online, make sure to schedule a free dating coaching strategy session. Our experts can help you with your profile or any other online question.

find mr. right this year
  • This field is for validation purposes and should be left unchanged.

Sign up here for a powerful gift!

BREAKTHROUGH-to-LOVE Premium Coaching Session!

Limited time offer- Free



Tired of loneliness and disappointment in your love life or marriage? This will change everything...

As a relationship expert, I've helped thousands of women get the love they want-even when it seemed impossible.  I'm Dr. Diana Kirschner. You might know me from my PBS Special, seen me on Oprah, or have read one of my bestselling books.

I want to do everything I can to give you hands-on personalized support that will make a lasting difference.

That's why I'm excited to offer a FREE 40 minute Breakthrough-to-Love-Coaching Session via Skype, Zoom or phone.

During your powerful and dynamic one-on-one session, we will help you with your unique relationship or dating situation. You'll walk away inspired, with a clear step-by-step path forward to move through any obstacles and get the love you want.

Here's what women like you are saying:

"My session was an incredible game-changer! I was finally able to see a way forward with my boyfriend and he has proposed!

I'm very grateful!" -Jenn in New Mexico

matchmaker, dating coach, dating tips, dating & relationship advice"I was fifty-two years old with a career that was enviably successful. But my love life was not. And I couldn't figure out why. As my love mentor, Diana helped me understand that I not only deserved to have but could have a strong, loving life partner who would always be there for me.  I found true love in three months! And after 4 plus years of marriage, my husband and I still pinch ourselves every day to make sure that it's not a dream!" - Midge Woolsey

Leave a Comment