16 Online Dating Do’s and Don’ts (especially for men)

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With more people than ever flocking to apps to find connection, now is an ideal time to get your digital dating dialed in. Here are some tips to bring your match-total up while you hunker down—from your friendly neighborhood dating coach. 

DO Use a High-Quality Photo for Your Primary Picture

This is a game-changer. Your featured photo is the first thing people see, so you have to hook their interest instantly, or they’ll move along. What works best? A flattering, quality portrait that gives the other person a good look at your smiling mug. Too many people make their faces hard to see, obscuring them with poor lighting. 

Since you likely can’t hire a professional snapper without violating social-distancing rules, look for the best existing portrait you have. Or, if you’re quarantining with someone, have them snap a photo of you—keeping in mind that natural light will make you look best. Bonus points if they know how to use light and photo filters to amplify your attractiveness.

Finally, choose your top three portraits, and ask friends to pick their favorite. You can also post shots on Photofeeler.com to get unbiased feedback.

Once you have a bright, flattering portrait that stops League swipers in their digital tracks, you’re on your way to a LOT more matches.

DO Add Video to Your League Profile

Still photography? That’s SO 2019. The League now lets you upload a video (up to 10 seconds in length) to your profile, allowing you to more vividly display your awesome personality. Whether you’re flirting, laughing or singing (yes, there’s audio, too), you’ll now have an edge over those who only use photos. As a bonus, the app’s algorithm prioritizes profiles with video, boosting your visibility and yielding more matches. Pro tip: For the most dynamic videos, feature an activity, such as water-skiing, shooting hoops, hitting the beach or petting your pooch. Press “record” for more matches and dates. And… action! 

DON’T Post Low-Quality Selfies

Using selfies as the featured photo is the number one reason why perfectly dateable people struggle with online dating. 

As I tell my male clients, “Guys, it’s not you — it’s the photo of you in your bathroom mirror.”

Selfies are almost always poorly lit and are about as flattering as cargo shorts. Singles wade through a sea of selfies, so even a “good” one is forgettable—and forgettable photos hurt your results. 

DON’T Sweat a Flake

If someone cancels plans with you, avoid over-reading the tea leaves. People get busy, or overbook themselves. Be open to giving someone a free pass for flaking. Use it as a chance to be awesome, not bitter—and you might end up with a date. 

How? When they flake, reply with humor. Write something like, “Why isn’t there a sad sunglasses emoji to show I’m bummed but still cool A.F.?” Or perhaps, “Hey, no problem—you just have to be twice as fun next time.” 

Or my personal favorite: “Unsubscribe.”

DO Show Your Face Clearly in All Your Photos

This will boost your odds of a match by about 20% studies show.

Bonus tip: speaking of faces, don’t include a prettier face than yours on your profile. I have a handsome, male-model-looking buddy, and I love the guy—but no way do I need to be competing with him on my profile.

DON’T Make Your Profile Sound Like a Resumé

And avoid groaners that you’d hear on “The Bachelorette” (e.g., “I just want to make a connection…”). A weak profile write-up can sabotage a great primary photo.

DO Give Your Profile Some Personality

Crack a joke. Share your favorite Dave Chappelle quote. Be cheeky. 

I fell madly in League love with a profile that began with this line: “I want a gentleman in the sheets and a dad-bod on the streets.” I couldn’t write her fast enough…she had me laughing so hard. 

DON’T Open With “Hey”

Or “How’s your day?” “What’s up?” or any variation of “Hello.” It’s as boring as CSPAN and shows that you made no effort to capture their interest. Starting with “Hey” is akin to saying “Hey, would you please ignore this message and never date me?” And they will oblige.

DO Open with a Specific Compliment

Be specific and sincere. Look at their photos, read the description and their interests, and see what strikes you as quirky, interesting or cool. Maybe it’s their style, their fondness for Will Ferrell movies or their skills in the kitchen. Tell them what impressed you, and follow with a related question that’s easy to answer.

Bonus points if your question makes them an expert, or allows them to brag. (We ALL love being experts.) Something like, “Hey, NAME… you cook Italian food? So cool! OK, let me ask: What’s your most delicious dish?👨‍🍳”

DON’T Send Copy-and-Paste Openers

You want them to feel special, not feel like they’re on an email marketing list. 

DO Use Puns to Break the Ice

Puns get a bad rap. The 17th century English poet John Dryden called them “the most groveling kind of wit,” and it’s said that the Roman emperor Caligula (a guy known for extreme measures) had an actor burned alive for a bad pun.

But puns work on dating apps like the League. They’re fun and clever. Your photos and bio hook their interest, but it’s your words that seal the first-date deal. So pun it up.

In “Romeo & Juliet,” a dying Mercutio says, “Ask for me tomorrow, and you shall find me a grave man.” If puns are good enough for Shakespeare, they’re good enough for you.  Don’t sweat it if you lack the Bard’s way with words. This pun generator can help you craft punny openers that get replies. Dads are good resources too. 

DON’T Send Messages Containing Spelling or Grammar Mistakes

The same goes for your profile. You don’t have to write like Hemingway, but you should know the difference between “your” and “you’re.” Otherwise, “your” dating life is gonna suffer. 

DO Move Things to a Call or Video Date ASAP

Most people wait too long to go for the digits or a date, which makes them seem either afraid of rejection or wishy-washy. My clients follow my 10-Message Rule. After 10 combined messages, go for the digits (or, in this case, the video date). The League’s 1:1 Video Chat feature is an excellent and safe place to have a first video date. Keeping virtual meets-ups in the app, especially early in a relationship, eliminates the exposure of exchanging personal phone numbers, Skype IDs or email addresses. 

DO Go On Video Speed Dates

Speaking of video dates, if you haven’t already participated in League Live, DO! Video speed dating is, first of all, fun (hello, human contact!). Secondly, it is safe (and convenient). But most importantly, the match rate for participants is three times higher than it is on the rest of the app. So if you feel like you are striking out in other areas, get online for the next League Live on Wednesdays or Sundays at 9pm. 

DON’T Be Afraid of “Ghosts”

When someone goes quiet, it’s no biggie. Expect it now and then. Ghosting goes with the territory. It’s not personal. It’s online dating.

DO Flirt When You Message

But—this is for the guys—avoid being overtly sexual. Getting too sexy-time too soon is a turn-off. However, a flirtatious touch does help spark chemistry, so feel free to sprinkle in some double entendres and innuendos. Some cheeky wit does wonders.

A client of mine recently matched with his dream girl—a smart, beautiful power-lawyer. The opening line that got him a host of heart-face emojis and a first date? “Counselor, you have a rebuttal that just won’t quit.”

The prosecution rests.

Connell Barrett is a dating coach in NYC, an advisor for Ask Men, and the founder of DatingTransformation.com. Follow him on Instagram at @datingtransformation.

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