How To Start A Conversation During Online Dating

Online Dating Conversation Tips

The Online Dating Introduction

You are browsing online and you find a profile that really piques your interest. Now what? They say first impressions are everything which means you have a lot riding on this first introductory message. Sound like too much pressure? It doesn’t have to be. Crafting the perfect introductory message for online dating can be quite easy if you just follow these tips on how to start a conversation during dating online:

dating online

❏ Read Carefully. Ensure you read the profile carefully and make mental notes of what you like about it.

❏ Identify Common Ground. Is there a photo that was taken at one of your favorite travel destinations? Maybe you share an interest in true crime novels. Finding areas of common ground is a great place to start.

❏ Personalize It. Personalizing your introductory message by noting various aspects of the person’s profile and then relating them back to yourself allows you to both show that you are truly interested and share something about yourself at the same time.

The Conversation

You’ve taken that first step and sent a thoughtful, well-composed introduction, and you got a response. Success! What next? Those first few exchanges are a key part of how to start a conversation during online dating and informing whether or not the person is a viable potential love match. What you want to do is balance the line between strategy and organic discourse. Here’s how:

❏ Keep it Light. It’s ok to ask someone what they hope to get out of the site, ie. a relationship, casual dating, etc., to gauge if you are on the same page, but be sure not to come off too strong with a line of interrogation-style questioning.

❏ Don’t Overdo It. Correspondence is vital to get an initial feel for a person before meeting in real life, but don’t wait too long. Doing so could cause the conversation to fizzle out or result in disappointment as you may meet and discover that you lack the chemistry you thought you had online.

❏ Watch for Red Flags. Those initial messages back and forth are the beginning of getting to know someone. Although some things are less obvious while talking online than in person, always be aware of anything that doesn’t seem quite right. It is much easier to misrepresent yourself online, something that is important to remember in thinking about how to start a conversation during dating.

Transitioning to the First Date

The conversation is going great and you are really enjoying getting to know the other person. You have now reached the point in the conversation where you are ready to take things to the next level and meet your love interest in person. This is great! How do you transition the conversation from online to offline? Read on to learn the final step in how to start a conversation during dating online that results in that first date.

❏ Get to the Point. Unless otherwise stated, neither of you are on the site just to find a new pal. You both know where this is leading. If the other person hasn’t already taken the lead, just go for it! Suggest that you meet in person and keep the conversation going there.

❏ Offer a Suggestion. Gauge their interest in a first date activity. Perhaps you have already discovered a mutual interest in art so suggesting coffee followed by a visit to a museum could be a great option and a great way to naturally segway the conversation to the potential of a face to face meet-up.

❏ Relax. It is completely normal to feel a bit nervous about not only the prospect of making the move to ask your love interest to meet in person, but also actually going on the date. Just remember that you are both in the same boat and enjoy the process as the person on the receiving end of those messaging could just be the love of your life.



  1. John Rivera

    October 25, 2016 at 2:22 am

    Very useful information. I like how everything is straight to the point and it really helps drive it home. I’ve had some problems in the past trying to express myself correctly when it comes to online dating. Next time I’ll put some of these tips to use, hopefully I see some success!

  2. Alanna

    October 25, 2016 at 2:52 am

    There are a lot of good tips here. I think it’s important to be yourself in order to possibly be matched with people you have things in common with. Adding a little humor is usually good too.

    • Melanie Nichols

      October 25, 2016 at 3:50 am

      Good points.. thanks for adding them. Best to you!

  3. Terri Smith

    October 25, 2016 at 7:05 pm

    Yes, online dating can be very tough! Even if some of this is obvious it is good to get a reminder. Reading this makes it all easier to deal with and understand. It is definitely a good idea to watch for “red flags” because there are a lot of nutty people on those dating sites. However, there are good ones too. This article can really help people find the good ones 🙂

  4. Leonard J

    October 25, 2016 at 8:03 pm

    I like how you mentioned how it’s important to be specific and personal in your messages, and to make concrete suggestions on activities – the first is important because it shows the other person you are really interested in them and not just a bot or spammer, and the second one helps move the conversation along to the next step. Good advice!

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