Do you struggle with starting conversations when online dating?

There’s something about dating that brings everyone back down to base.

Even though dating is still basic human to human interaction, there’s an emotional element(s) that puts people on edge. It’s vulnerability at its finest.

Are your nerves on edge when talking to a new colleague at work or the person at the grocery store deli counter?

However, when you break it down, you are an adult and your date is an adult. Two adults who are capable of managing conversation for an hour or so.

We talk to other adults every day who we don’t regard in a romantic fashion, and without the element of romance, conversations are typically easy going and undaunting. But, wondering if you’re talking to the love of your life, add mixed emotions and maybe a bit of turmoil. 

Here’s a typical scenario:

You’ve spent a few days texting back with a date and feeling good about the potential of this (maybe) blooming relationship. Texting convo felt easy and flowed nicely.

Now, you’re headed to meet this person face to face and you’re wondering how it’s going to go when you’re actually in each other’s company. What do you talk about? How do you make sure to keep the easy flowing conversation flowing in real life?

Here are some tips and tricks to keep in mind which will help you relax and avoid awkward silences and twiddling thumbs.


Ask open-ended questions. Try to avoid questions that yield  “yes” or ” no” answers.

For example:

Do you like chocolate ice cream?
     Yes. Or No. 


What’s your favorite ice cream?
     Soft vanilla cone with chocolate sprinkles. I like to keep things simple. But, I can definitely go for a brownie hot fudge sundae once in a while.

Build rapport by remarking on shared/similar experiences.

Perhaps you both backpacked through Europe once, or you both enjoy finding new destinations to hike, or you both love going to theme parks.

For example:

I remember you sharing in your profile that you love roller coasters. Me, too! The last time I was on a ride, though, was in Disney World with my family five years ago. I definitely need to plan a trip soon….

Keep conversation light and breezy by not bringing up controversial topics such as politics, religion, personal finances, past relationships and perhaps family history.

Obviously, you want to understand where your differences lie, but there is more time to get to that. On a first date, try to avoid polarizing topics and creating discomfort.

If something like this does come up, gauge your comfort level as well as your dates. If you sense something is off, change the subject, or share that you’d rather save a particular topic for another day. 

For example:

Tell me about your last date.
     More often that not, your date is not going to want to talk about their dating life


What is something you learned today that you didn’t know before?
     This is more lighthearted, fun and intriguing. 

Once conversation is going, make sure to employ your active listening skills. Be in the moment and be engaged. Ask follow-up questions, make eye contact, put your phone away.

There are also open-ended ways to stay engaged, keep a conversation going and have a lively discussion. 

  • Tell me more about that
  • Interesting Point
  • That reminds me of….
  • How did that make you feel?
  • I appreciate your opinion on that

If you want to start a conversation that has some fun spirit ask questions such as

  • What’s one thing you’ve changed your mind about in the past year?
  • What kinds of things light you up?
  • What is some of the best advice you’ve ever received?
  • Have you ever learned any lesson the hard way?
  • What are some of your favorite life experiences? 

Rule of thumb: Don’t ask questions you wouldn’t want to answer yourself – if you are hoping for vulnerability, don’t be afraid to be vulnerable yourself. 

Try to relax and be yourself. Always be yourself. There is nothing more impressive than a person who’s comfortable in their own skin and doesn’t try to impress. For more on this topic: Making A Good First Date Impression.

Also don’t put too much pressure on yourself. I like the concept of a “pre-date.” The first meeting should be easy going and introductory. You don’t have to worry about what the future holds. Live in the moment and get to know the person you’re talking to, the other human. Thoughts On Planning The First Date.

Above all, have fun!

Interested taking a deeper dive into the art of conversations? A great book I read is: How To Talk To Anyone.
Learn simple tips to help boost your confidence and have better more engaging conversation. There’s even a chapter on how to utilize your smile and how to use your eyes to make someone fall in love with you.

If you are interested in learning more about vulnerability, Brene Brown is an industry leader on the topic. You can start with her book, Daring Greatly.

Book links are affiliate links. This means that, at zero cost to you, I will earn an affiliate commission if you click through the link and finalize a purchase. This is how I keep my blog ad free. 

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