How to Not Suck
At Online Dating

Men in online dating are usually split into two categories. Those who seem to succeed with ease and those who struggle endlessly. Both sides have no idea what gets them those results.

I set out to understand this disparity. Since my last online dating article (almost 2 years ago!), I’ve re-worked dozens of men’s profiles and re-written hundreds of messages. Here are my collective findings to take your online dating from frustrating to fulfilling.

Profile Photos

Take your pictures seriously! I can’t say this enough – pictures in online dating are everything. They’re more important than the words in your profile and even your messages.

I’ve already written an extensive guide on taking attractive photos, yet every guy I work with for online dating has terrible taste in pictures.

Women get dozens of messages a week. You need to stand out. Without flattering pictures, women won’t even open your messages or take a deeper look at your profile.

You don’t need to be amazingly attractive. You do need to find photos that present yourself in the best way possible.

  • Search your computer and social networks. Whenever I work with an online dating client, I ask them to find other pictures not currently on their profile. They send me photos from Facebook, Instagram, digital cameras, and hard drives. We almost always discover better pictures than what they’ve uploaded to their dating profile.
  • Choose only clear, high-quality shots. Discard all low resolution, grainy, washed out, off-color photos. Pictures that used flash usually do poorly as well. I don’t care how much you like the content of the picture, if the quality sucks, get it out of there.Your main photos should be taken with a good point-and-shoot camera, recent smartphone, or preferably a DSLR. Even OKCupid’s studies have shown how much of an impact this makes.
  • Pick photos where you’re dressed well. You don’t have to be wearing a dress shirt or a designer outfit. But your clothes should be fitted and match accordingly.
  • Do basic touchups. Seriously, why are every guy’s pictures not edited? It takes one minute and makes your photos instantly better. Whether that’s on your smartphone, computer, or even with a free web-based application such as Pixlr.At the minimum, use the “auto-enhance” or “auto-correct” functions. Use the shadows and highlights functions to remove any dark or over-exposed areas.And please, crop your photos to the main content — yourself. Unless the photo is supposed to be a distant landscape shot, remove any distractions. No one cares about the 5 feet of ceiling above you, the empty space to the sides, or the clutter in the room.
  • Submit your pictures to MyBestFace. What if you had a data-driven way to find out exactly which of your pictures women find most attractive? Wait, you do — and it’s free!OKCupid’s MyBestFace has women rate your pictures and rank them from best to worst. Stop guessing and start finding out what photos you should be using on your profile. Repeat if necessary to confirm the findings.
  • Pick the best close-up photo for your main picture. Photos where you’re smiling at the camera or looking away from the camera without a smile tend to be the strongest. This has been confirmed by OKCupid’s study as well as my personal findings over the years.Adjust the thumbnail box as close to your face as possible. You want a clear headshot to draw people in as they scroll through profiles.

Profile Content

Compared to the importance of your photos and first messages, profiles come last. They’re mostly used for women who read your messages and are on the fence. Having a decent, non-threatening profile is all you need.

It also helps to have a bit of personality and specific details about you. That way she has something to comment on in her response.

  • Keep it positive and exciting. Complaining, cynicism, pretentiousness, self-deprecation, and overall negativity turn women off. Being passionate about your life and who you are is attractive. You want to entice women to be a part of it, not scare them off.
  • Eliminate excessive swearing. It doesn’t make you sound cool. It comes off crude and intense. You can drop in a curse word if it truly adds emphasis to a story or a point.
  • Explain your job in relatable terms. Keep the technical talk to a minimum. Instead, focus on how it benefit others or express why you’re so passionate about your career.Bad:“During the day I work with scientists and software developers at a bioinformatics research lab. We focus on ways that the discipline of informatics can directly contribute to medical diagnoses and treatment. I work on software that runs our sequencing pipelines, create visualizations for scientific publications.”There’s just too much factual detail here. This isn’t supposed to be a resume. Save the specifics for the date.


    “I work on software that makes complicated medical data easier to visualize and understand. Our research helps doctors diagnose and treat patients more effectively.”

    Simple, easy to relate to, and intrigues her to know more about your career.

  • Be specific. This makes you different than the million other guys listing the same generic stuff. It also gives her content to comment on. For example, if you were to list some of your interests…Bad:Sports



    Cheering on the Patriots on a Sunday afternoon
    Spicy Tuna rolls from Sushi Chef
    Quality time with my sisters and nephew

  • Speak with emotions, not just facts. Another variation of this is “show, don’t tell.” Think about the “why” behind your hobbies, interests, and passions. What motivates you? What excites you? What do you love?Bad:“I am a good listener. I consider myself to be very open and honest. I’m a pretty ambitious and loyal person for many reasons. I’ve also been trying to do standup comedy in my free time.”



    “I’m a good listener and I’d like to think it’s because I love hearing people’s stories — what they feel and what makes them who they are. I can be direct and to the point but always compassionate.

    Loyal and ambitious, my father’s work ethic has always inspired me to make a difference. 

    I’ve also been facing my fears by doing standup comedy. I enjoy acting and pushing myself to get into a character’s head.”

  • Position yourself as a potential romantic interest. Women use online dating sites to find men they might date. They’re not looking for a new male bestie. Get rid of anything about being her friend, requesting recommendations on restaurants or food, or offering to be a tour guide.
  • Remove your income if it’s low. Leave it blank or choose the “I’d rather not say” option instead. I’m all about being honest and upfront with who you are. But I also understand basic marketing principles.Some women automatically overlook men under a certain income bracket. Those same women would be open to connecting with you if given the chance. Don’t eliminate yourself before she’s had the opportunity to be attracted to your other qualities..
  • Be the buyer, not the seller. Don’t try to prove why you’re good enough. Don’t beg for a woman to like you. Nobody finds that attractive.This most often comes up at the end of guys’ profiles. They write stuff like, “You should message me if you want to or think we’d get along.”Instead, be challenging and list some qualities you want in a partner. “You should message me if you’re someone who’s not afraid to push yourself and do silly things with me – whether that’s singing karaoke or dancing in the streets.”

First Messages And Follow Up

I’ve found the most effective messages follow this basic formula:

1. Joke / humorous observation from her profile or photos / tease / playful flirtation
2. Open-ended emotional question. (optional)

This structure works with minimal effort. You should be able to send off a great message in under 5 minutes.

Reference my article on captivating first messages for more guidelines and examples.

  • Send out way more than you think. You can write the best messages ever and a lot of women won’t reply. In fact, I don’t think I’ve seen a guy consistently get over a 40-50% response rate.Online dating for men is a number’s game. If you aren’t sending at least 5-10 messages a week, you aren’t going to see much success.You have to stop waiting for women to reach out to you first. And if she does “like” your profile, that’s her saying she wants you to message her. Stop making excuses that you don’t have the “perfect” message to send. Because all that time you spend waiting, she’s getting messages from other guys.Don’t take it personal if you don’t get a response. You can’t let anything deter you from sending out messages regularly.
  • Make your messages fun. Your #1 priority in online dating is to convey that meeting up with you will be a positive, enjoyable experience. That’s it. Showing how you’re a great fit and share similar values comes second and often can be saved for a first date. You simply need to reassure women that a date with you will not be intense or awkward.The easiest way to accomplish that? Humor. If you can make a girl smile or laugh when she reads your message, your chances skyrocket. Laughter is the quickest way to get someone to drop their defenses.Many guys understand this concept but it stresses them out. They worry about trying to figure out how to make girls laugh online. But that’s the opposite way to think about it.The trick is to focus on making yourself laugh! Because if you’re genuinely having fun with the process, she’ll pick up on that and have fun, too. When crafting a message, my thought process becomes “Would this make me laugh? Is there a joke? Is it lighthearted, silly, or playfully challenging?” If the answer to any of these is a yes, I know I’m on the right track.
  • Tailor them to each profile. Generic messages have the lowest response rate. You need to reference something specific about the girl you’re talking to.My method is to quickly scan a profile, find one or two points that genuinely interest me or make me laugh, and write my humorous message off those.
  • Keep them short both in length and wordiness. 1-4 sentences are more than enough to make a strong impression. Cut out excessive words that aren’t important to the core of the message.Bad:“You should never have to apologize for your passions to anyone. Personally, I think reading is for the cool kids.


    I like to read a lot over the summer. So what fictional book world are you escaping to currently?”


    “Never apologize for your passions! Reading is for the cool kids.

    What world are you escaping to currently?”

    I removed all the excess while still keeping the same message. The fact that you read is already implied. Also, the specific time of “over the summer” doesn’t matter and isn’t relevant.

  • Double-check your grammar and typos. Use spell check. Don’t let a simple mistake eliminate you before you get a chance.
  • Give her something to respond to. This usually comes in the form of a question at the end of your message. Even if a girl’s interested, you want to make it easy for her to reply.This should be relevant to something about her and follow the basic guidelines from my article on mastering conversations:Make it open-ended so she has to give you a more honest, deep answer. Try to ask something creative or unique so she hasn’t heard it a million times before. And frame it in a way that evokes emotion from her – that could be passion, nostalgia, or humor.
  • Push to meet up soon. Go for it by your 2-4th message. Don’t forget the entire point of sending messages: to setup real-world dates.I know when you get a reply the attention feels good. Maybe you’re afraid to screw it up or hear a rejection. But if she likes you, she wants to meet up. I see too many guys hook a girl’s interest only to stop getting replies because they didn’t push forward.When suggesting to hang out, offer a concrete plan. This can be as simple as drinks, ice cream, an outdoor hike, or something you both have in common from your profiles.Assume she wants to meet up and don’t ask her if she wants to see you. Sound confident in the adventure you want to have with her. Don’t say you can do whatever she wants or give her a dozen options.


    “Do you think you’d want to meet me in person? I understand if it’s too soon. Maybe we could get a drink or a coffee or take a walk or something. Or if you have any other ideas, too. I understand if you want to meet in a public place or if you just want to keep talking.”


    “Wow, you just actually made me laugh out loud — bravo. We should continue this over drinks. Are you free Tuesday?”

Want to up your online dating game? Get expert advice on your profile.