5 Rules to Succeed at Online Dating (A Guide For Men)

This article was first posted on The Good Men Project.

Last week, I bumped into a friend Nick on the subway. 

Nick is single and a fantastic catch for the right woman. At 40, he is an executive manager in a small not-for-profit that works on educational reform. Highly intelligent and quick-witted, he makes conversation effortless and has an infectious laugh. In his free time, he plays soccer competitively and is in better shape than men half his age. 

The problem? 

Nick is Indian-American and 5’6” tall. Online dating has left him feeling as if he’s not quite up to snuff. 

“I’m feeling pretty despondent about my love life these days,” Nick said during our conversation. “Despite my best efforts, women are not clamoring for the short Asian man.” Nick’s frustration was palpable. And, it broke my own heart. 

Can a great catch succeed online when the forum overwhelmingly lends itself to superficiality? 

The answer is yes.

During my single days, I dated prolifically and can attest that certain qualities elevate a man above the competition:

1.    A great profile picture.

Online profiles with pictures get 10 times as many looks as those without. Profiles with quality photos get 4 times as many glances as those with poor photographs. 

A picture really is worth a thousand words, so it behooves you to have a great face and full-length picture. (As tempting as it may be to post that bathroom selfie, please refrain. Trust me, even Brad Pitt looks less than desirable with a toilet beside him.) 

Digital technology makes it easier than ever to capture 1-2 great photographs. Hire a professional photographer or enlist a friend to take 100-200 pictures in an interesting location on a beautiful day. You’ll be guaranteed to have a picture that makes you feel confident and proud. 

2.    An interesting profile.

Everyone in the world has a story to tell. Yet, the majority of online profiles could put an insomniac to sleep.

Stand out from the crowd by telling a story that piques the reader’s curiosity. Here are a few examples of great opening lines:

  • "In high school, I wrote an underground newspaper that exposed my principal for plagiarism."
  • "I make the best French fondue from my Nana's recipe. If you twist my arm (and bring a baguette), I may even tell you the secret ingredient."
  • "In 2008, I spent a month living in Uruguay. It was awesome, except for one thing..."

Keep it short and simple, but make the reader want to learn more.

3.    A willingness to fail often. (And, take calculated risks.)

Several years ago, Edward approached me on the subway and asked for my number. We went on a few dates and while there was no romantic chemistry, we remained good friends. I respect something very unique about Edward—his willingness to fail often with women. Through failure, he explained, he improves his “game” and becomes less risk-averse (i.e., the sting of rejection hurts less each time).

To me, this is the attitude of a winner. 

Get in the game. Instead of passively “winking” or looking at women who interest you, drop them a line. 

According to OkCupid, the most attractive women receive 5X more email than average women and 28X more email than unattractive women. 2/3 of male messages go to the best-looking 1/3 of women. Statistically, the average male sender gets a 27% reply rate from the most attractive females.

If you’re messaging the most attractive women, your competition will be intense. And, you have a fairly small chance of receiving a response. Knowing this, you have two choices: 1. risk repeated failure (and frustration) by continuing to play the game like the majority of people, or 2. expand your mindset and reach out to the 2/3 of women who are otherwise being “overlooked.” Or, you can play the odds and do both. 

4.    Sincerity. Honesty. Confidence.

Attractive women with good profiles have a profusion of suitors. But, quantity does not equal quality. Rise above the pack--be the one person who writes a thoughtful, sincere and funny email that engages her on a personal level.

Read her profile and reference something contained therein. Keep it short and simple (and grammatically correct). Close with a question that begs a response. For example:

“I love Bill Murray movies, too.  Would you agree that “Rushmore” beats “Caddyshack” hand’s down?”

You’ll bait conversation, as she will either be in vociferous agreement or challenge you to a fight. Either way, you have an opening. And, whatever you do, leave all sexual innuendo at the door. 

5.    A (great) plan.

Within 3 email exchanges, ask for an actual date.  Be specific and clear in your intent. (There’s a big difference between “Hey, we should chill sometime” and “I have two tickets to the Brooklyn Nets game Friday night. Want to go?” Aim for the latter, not the former.)

Dinner and drinks are standard, but won’t make you memorable. Instead, plan a fun, interactive date (that allows for conversation without a lot of pressure). Some of my best dates were also the most unusual, including:

  • A BYOB painting class.
  • An orchid show at the botanical gardens followed by oysters and cocktails.
  • A walking tour of Chinatown and dim sum.
  • A class on Japanese and American whisky.
  • A bike trip with various stops for food and wine. 

Take the lead with confidence. Show up on time. Open doors. Pick up the tab, even if she offers to share the expense. (Nothing kills romance faster than haggling over money.) If you had fun, suggest a follow-up date that day.

In a world where money and looks are deemed “exceptional,” aim for the even rarer qualities of chivalry and class. You’ll be sure to stand out in a sea of mere mortals.






Monica Parikh