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20 Ways to Make Being Single Fun...and Dating a Little Less Sucky

May 1, 2013 at 3:56 PM ET

20 Ways to Make Dating Fun and a Little Less Sucky
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20 Ways to Make Dating Fun and a Little Less Sucky

Throw a Profile Party

Gather up your gal pals, pour some Pinot Grigio and get typing. Like a bachelorette party before a wedding, throw a fiesta before you take the plunge into digital dating, proposes cyber dating expert Julie Spira, author of The Perils of Cyber-Dating: Confessions of a Hopeful Romantic Looking for Love Online. “Often you get too close to yourself,” she adds, “and you don’t see your amazing traits.” Enter your BBFs, who can help you brainstorm a pitch-perfect profile ideas and set up a DIY photo shoot to capture some come-hither pics.

Go on a Hunt

Let’s face it, you’re always on the prowl for Mr. Right, even if you tell yourself, “I’m just going to have fun tonight.” So instead of pretending you’re not looking, make it a true pursuit the next time you and your friends walk into a bar. Compile a goofy scavenger hunt list with items like, “get a bearded fella’s phone number” or “buy a drink for the guy flying solo.” Plus, it makes an easy-peasy ice breaker and an instant convo starter, so you don’t have to freak out about making the first move.

Play the Dating Game

Want a surefire way to score with online dating? Turn it into a competition with your friends. No, we’re not talking Hunger Games style, more like fantasy football inspired. Keep the rules simple: 1 point for every 5 winks you receive, 2 points for every 5 messages, -1 point for every "no thanks” you get (wah-wah) and so on. The prize is, of course, everlasting love... or a night of free drinks. And may the odds be ever in your favor!

Dress the Part

You know how they say if you buy cute workout gear, you’ll be inspired to exercise more and actually like it? Well, the same can be said for dating. If you’re newly single or just want a fresh start, treat yourself to a mini makeover. Invest in a killer first date outfit or try out a new hairstyle or simply buy sexy skivvies. That small dose of retail therapy can get you motivated to flex your love muscles.

Take It Offline

Don’t get stuck in a lengthy back-and-forth messaging marathon with a potential online date, cautions Jessica Massa, author of The Gaggle: How the Guys You Know Will Help You Find the Love You Want. Aim to meet in person as soon as possible to determine if there’s chemistry, recommends the author. That way you can quickly move on if there’s no spark in real life. Or skip the winks and what-not altogether, and attend a group event organized by an online dating site, like Match.com and OkCupid, and mingle with other eligible members.

Cultivate Your “Gaggle”

The “gaggle” concept, coined by Massa and her best friend/business partner Rebecca Wiegand, refers to “the group of guys in your life who you might not be dating, but who play different roles, fulfill different needs and help you figure out who you are and what you want.” That could include your coworker, your crush, even your cute barista. The key is to not look at every guy you meet as a potential soul mate, says the author. Instead, nurture the relationships (whether romantic or platonic) and learn from them.

Write About the Mr. Wrongs

“Awful dates make great stories,” says Starshine Roshell, the “Tough Love” columnist for TheWeek.com. To help view your manhunt as an epic romantic comedy (with a happy ending, of course), she suggests writing about your dating disasters and singleton successes in a private journal, on a blog or with brutally honest tweets. Digesting and expressing your thoughts -- even if it’s in just 140 characters or less -- can help you pinpoint the hits and misses in your love story.

Try Safety in Numbers

Classic single sitch: You’re totally lovable around your friends, but are painfully awkward on a one-on-one date. Solution: Enlist your best buds and their dates to help relieve some of the pressure and put you at ease. Or sign up for Grouper.com. The site matches you and two of your friends with a group of three dudes for a drinks outing. The more the merrier, right? Or misery loves company....

Flip the Script

Do all your ex-boyfriends look like they came out of the same man candy factory? If so, you might want to try dating beyond your type. For instance, seek out an older worldly gentleman instead your usual all-American boy. Or ditch the regular hard-partying rockers for a quiet, bookish fella. The change of pace may be enough to jumpstart your stalled love life and give you a new perspective, even if you go back to your usual cast of characters in the end.

Get Crafty

Nope, we don’t mean homemade Valentine’s Day cards here. We’re talking about finding your inner Oprah and creating a vision board depicting your perfect man and relationship. (FYI: Ryan Gosling enjoying long walks on the beach is already taken.) Cut and paste images, quotes, anything inspiring to an old-school bulletin board or go digital with Pinterest. As you date, add and remove items to get a clearer picture of how you see your romantic future.

Book a Bunch of “Non-Dates”

For better or worse, dating ain’t what is used to be (sigh). Men and women are connecting in more ambiguous ways, explains Massa. Out are the traditional dinner-and-a-movie dates, in are after-work drinks and random hangouts, which offer up lots of lovey-dovey possibilities. Fortunately, this new way of mating means your love life isn’t totally MIA (yay!) even if you don’t have plans with a man on Saturday night. But it also means you need to say yes to spontaneous invites and no to couch time with your cat.

Celebrate Your Single Self

“Don’t waste your unattached time being anxious and longing for the day when you’ll be in a relationship,” says Massa. Instead, indulge in SSB aka single-self behavior (thanks, “Sex and the City”). Watch “Pretty Woman” for the 100th time. Go to the bathroom with the door open. Enjoy the other kind of self love (well hello, vibrator!). Whatever it is, make the most of your “me” time because if you don’t want to hang out with yourself, why would a man?

Be a Teen Again

In the beginning, dating was all about your giggly school-girl attraction to some boy. You didn’t care if he had a car, a 401(k), a job, a future... Take a page out of your teenage diary, ditch your grown-up relationship checklist for a minute, grab your date’s hand and get a slice of pizza. Or drop some quarters at the arcade. Or make out like bandits on the couch -- remembering what it’s like to like someone just because. Plus, there’s a practical twist: teen-inspired date ideas are usually easy on the wallet!

Download Love

Sadly, Siri can’t score you a date, but a slew of location-based apps can play the role of a tech-savvy Cupid. Dubbed the straight version of Grindr (but more than just a hook-up finder), Blendr connects you with local singletons on the go, while OkCupid’s mobile app lets you broadcast and browse nearby activity suggestions and message a member if something catches your eye. Similarly, HowAboutWe allows you to post and respond to date ideas based on where you are.

Suggest a New Spot

Dying to try a different sushi place? Or a buzzed-about bar? Suggest it as the meeting place for your first date, advises Massa. The guy may only get a one-star review, but at least you got to test out someplace new. Remember to keep tabs on which joints you liked, and designate which ones are perfect for a romantic table for two or for bigger group dates. This makeshift Zagat’s guide will definitely come in handy for future date-making.

Sign Up for Something

Join an organization, take a class, volunteer for a charity or sign up for a sports league, suggests Massa. There’s a reason this is an oldie-but-goodie dating tip. It allows you to meet a like-minded guy in a casual, pressure-free setting, explains Massa. Plus, you’re possibly learning a new skill, and adding to your awesomeness. “What guy wouldn't be enchanted by a concert-going, dog-training sailor woman?” asks Roshell. Indeed.

Take a Lesson in Love

Want to fine-tune your game? Hire a dating coach to review or create your online profile, recommends Spira. Experts, like Spira, know the ins and outs, buzzwords and digital strategies to catching a mate through the interwebs. You can also enroll in her extensive dating boot camp, which includes coaching sessions, email critiques and pre- and post-date support. Or for the analog among you, sign up for a body language class, like Blake Eastman’s dating workshop in New York, which teaches you how to master and decipher those flirty nonverbal cues.

Think Outside the Box

These off-the-wall dating methods will spice up your search and make one helluva “how we met” story: If you live in a big city, "reverse commute" to the burbs for eligible men. Traveling by air? Submit your flight info and departure destination to MeetAtTheAirport.com to be matched up with a fellow passenger. Or date your doppelganger, thanks to FindYourFaceMate.com, which pairs up folks with similar facial features. Then, let your nose lead at a pheromone party where singles sniff out attractive bodily scents. Finally, you can cast a love “spell” with Words with Friends; the app’s creator claims that 44% of its players have flirted with another competitor.

Stop Freaking Out

You may think the grass is always greener (and has a white picket fence) on the other side. But being the Debbie Downer of dating can be counterproductive. “If you put too much pressure on anything,” says Massa, “it becomes soul-killing.” Instead, take a deep breath, concentrate on all the romantic possibilities (not the missing pieces) and “see your love life as an exploration... not simply an end goal,” adds the author.

Choose Your Own Adventure

Whether you want to go surfing, hit the slopes or shake your hips while practicing your salsa moves, seek out a totally up-for-it dude with the same passions and interests. (Spira suggests joining a local Meetup group to find adventurous folks.) Your guy could be a total pro already or a newbie like you who wants to explore. Whatever the case, you’ll get to scratch another item off your bucket list (and maybe your, um, fucket list).

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