10 Ways to Initiate an Online Conversation

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Lots of people struggle with making conversation.

Beginning a conversation on a dating site can seem even harder. I know I struggled with what to say when I first joined CatholicMatch. I made some pretty big blunders and probably scared off a lot of women!

Looking back, I recall some obvious, beginner mistakes. I’d message a woman I liked and ask her out to coffee to get to know her—in my FIRST message. What can I say? I’m quite forthright—I just had to learn to have a few light conversations first, before asking someone out on a date.

Or, I would send someone a two paragraph message that basically summarized my profile when a simple, “Hi. I enjoyed reading about you. We have some common interests. I’d love to chat further,” would do. Needless to say, those messages never got any replies.

Over time, as I read advice on dating dos and don'ts, I got better at messaging women, evidenced by the higher percentage of women who responded back to my messages.

Need some ideas of ways to engage in light, beginning conversation? Read on.

So here’s my list to help those of you who are new to online dating. It begins with actually reading people’s profiles and paying attention to more than just the pictures.

1. If the person has already taken the personality quiz, read about their personality type and ask them what they thought of it. Did they find it to be accurate?

2. Music is a common language we all share. Ask about the musical interests that they’ve listed. If you both like the same artists, use that as a launching pad for conversation. Do you both like going to concerts? Enjoy dancing?

3. Pay attention to the places they’ve visited. Perhaps you’ve also been there and can share something you really enjoyed about that place. Or maybe you’ve always wanted to go there and would like to know what their experience was like.

4. Presumably, your faith is important to you. If the person is a convert, ask them some questions about what drew them to Catholicism. I’m a revert to Catholicism and I find people’s journeys to the Church fascinating. If I see that a woman converted to Catholicism, I almost always ask questions about what drew her to the Catholic faith.

5. Perhaps you have some hobbies in common. Do you both like the outdoors? Inquire about good spots to hike in their areas. Share your favorite spots.

6. Welcome newcomers to CatholicMatch. Help them feel at home. Reach out to them to inquire how their experience has been. Ask them if you can pray for them for a specific need.

7. Wish people well on their birthdays. Follow up to find out if they did something special on their birthday.

8. Comment on their photos. But please don’t comment on physical attributes. Even if done in good faith, it’s generally seen as being in poor taste. Do comment on travel pictures they might have posted that appeal to you.

9. Ask them a fun question that prompts a response. Ice breakers are not just for real-life dates... they can be quite helpful in getting the ball rolling with online conversations: "Hey Ella, if you had an extended vacation, would you rather travel overseas, or explore your own backyard?"

10. Write more about you. When you write your own profile, give people enough material to begin, or continue, a conversation.

Here's a dating challenge for you to put these suggestions into practice:

Send a message to at least three new people each day. Don’t let yourself be limited by geographic area or by some of the other filters you use. Expand your horizon a bit and see what happens.

Take initiative with these tips, and you'll soon be meeting new people and (hopefully) finding love!

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