How Long Should Messages to Online Matches Be?

Nick Slade

Written by: Nick Slade

Nick Slade

Nick spent 20 years in the dating scene before marriage. He has always been the guy friends would come to for advice on relationships, and he developed a knack for giving helpful insights. After college, Nick was a disc jockey for a few years, when the love generation was still alive, so Nick has a lot of relevant experience to draw from when it comes to every aspect of dating, falling in love and screwing things up. He holds Bachelor's degree in humanities and a slew of master’s credits in journalism. Nick is a news junkie and tries to keep up on the latest non-fiction when he has time. He has published two books on how to win at dating and relationships.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Advertiser Disclosure

Initial messages to an online match should be somewhat short, but they should be long enough to be meaningful and make you stand out. You need to:

  • Introduce yourself.
  • Endear yourself with a complimentary reason for your attraction to her.
  • Ask a question about a person, place or activity that might connect you.
  • Close the sale with a request and reason for her to respond.

Many sites allow you to send “winks” or prefabricated icebreakers, which most women totally disregard. It’s like a junk mail coupon for 1 cent off a box of crackers. Nobody cares and it gets trashed with the rest of the spam. A simple “Hey” or “What’s up?” will suffer the same fate.

If you send something too long and detailed, it will seem like an impersonal form letter that you send to all the girls, and it will not get you very far with most of them. They all have a full mailbox every day.

The key is to make it as unique, personal and concise as possible. This means that you have to make sure she can tell it was written especially for her.

Refer to something in her photo or profile that proves you have spent some time considering her attributes and have found something special about her that appeals to you, intrigues you, or makes you laugh.

“Eyes” and “smiles” are too generic. “Big green eyes that match your scarf” or “a sexy smile with one cute dimple on the left side” can only refer to her.

Three or four sentences is perfect, but make each one count.

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