5 Ways to Start a Conversation when Dating Online

Dating

5 Ways to Start a Conversation when Dating Online

As I match with guys on dating apps to find a date for my 50 Dates in 50 States journey, I get a range of messages. Most first messages don’t lead to a great conversation. They usually start with a compliment or a basic ‘How are you.’ When I have multiple matches it’s work to keep up with all the conversations especially if they are boring. If I am engaged and excited about a conversation I usually respond promptly. When it comes to dating it’s important to make sure your first message is engaging and intriguing, so the conversation doesn’t end before you have a chance to go on a date. Here are the 5 best ways I know how to start a conversation on a dating app.

1. Ask an Open Ended Question

The best way to start a conversation is with an open ended question. If you ask an open-ended it’s less likely you’ll get a one word answer. Figure out a question is to look at their bio and pictures and ask a question related to it. If you need question ideas click here for Big Talk Questions.

open ended question message

2. Use a Clever Pick Up Line

I LOVE a good pick up line. They can make you laugh or make you think a little. Most pick up lines aren’t super engaging though so don’t use basic pick up lines, be clever. Look at their name, bio, and pictures and create/find a pickup line related to it.

This isn’t a one liner, but this guy was really clever. He read my bio and saw that I was going to be in Houston, and came up with a pick up line. I don’t usually exchange my numbers with a guy that early, but I thought it was so clever I gave him my number.

pick up line message

3. Compliment Followed by a Question

Yes, a compliment is always nice to receive, but the conversation can always end quick after that. So make sure you add a question to that compliment…an open ended question!

compliment message

4. Be Random

Be random, but be yourself. When I’m tired of trying to figure out the best first message, I just rogue and send something completely random. The response to a random message really shows what kind of person you’re talking to. Do they think it’s funny? Are they a little rude?

A few years ago I actually started sending ‘I love you’ as my first to guys. Some would make a joke about it. Some took it seriously. One guy actually said ‘I love you’ back. We talked and exchanged numbers and actually went on a date. He was super sweet, but he just got out a long term relationship so he wasn’t looking for anything serious. It didn’t work out with him, but that random message turn into an engaging conversation, and turned into a date.

5. Be Bold and Ask Them Out

Sometimes having a conversation online is tough. Maybe your first impression is better in person. If someone’s profile has already convinced you that you want to meet them be bold and ask them on a date! Life is too short to be wasting time online anyways.

first message infographic

Need Help?

If you need question ideas click here for Big Talk Questions. 

If you want my help sending that first message DM on instagram for some help.

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