7 Smart Tips on How To Start Dating Again (and Come Out Winning)

Updated 10/02/19
A couple on a coffee date holding hands.
Soren Hald/Getty Images

Getting back into the dating game after experiencing a dry spell can be intimidating (to say the least), and even just a few months off can feel like an eternity.

Then, once you finally do dip your toes back into the dating pool, you once again face all the typical first-date jitters you loathed experiencing the first go-round. A whole host of conflicting feelings—like gratuitous excitement (Could this be the one?), negative uncertainty (Why am I doing this, anyway?), and crippling anxiety (What do I say? Or not say?)—can wreak havoc on one's constitution.

Starting to date again is especially difficult because you're allowing yourself to be vulnerable, opening yourself up to rejection, and offering up your fragile heart (and ego) in effigy. You might think your newly-minted openness has just as much of a chance to reap true love as it does the cold shoulder. But take heart: Getting back into the dating game doesn't have to be so spirit-crushing and gut-wrenching.

Here’s how to how to start dating again, with confidence, and come out winning. Because kissing a few frogs in the short term is definitely worth the journey (however lengthy) to find the love of your life.

make peace with your past

You won’t be able to start a relationship with someone new if you’re still hung up on that venture capitalist who refused to make time for you. Take all necessary steps to get over your ex: Grieve if you have to, or go on a dating detox, and then, relegate the past to ancient history. Only once you've taken the time to heal old wounds the right way—whether via talk therapy, time taken, or meaningful chats with good friends—are you then able to learn from past mistakes, thus fostering better future relationships. If you find yourself dwelling on your ex, stop your train of thought and remember the reasons why you used to love being single. Back then, you could do whatever you wanted and felt liberated at every turn.

mojo matters

Before you start dating again, do what you need to do to get your mojo back, whether it's vowing to change unhealthy dating patterns, adjusting your relationship priorities, or adopting a new, positive outlook on dating.

Remember: Confidence is an attractive quality. So, flirt with the cute barista, leave your number on a napkin for the beautiful chef who personally stopped by your table, and initiate contact with that tall drink of water you’re lusting over on Bumble.

Once you've gotten your groove back, the prospect of going out with someone new won't spark negativity or uncertainty. Instead, you'll remain hopeful and wide-open to new experiences once you start dating again. In turn, that hopefulness and positivity will show on your face, attracting dating prospects to you like bees to honey.

beautify

There's no way you'll feel sexy (and second date-worthy) if you don't allow yourself to feel beautiful. And pampering yourself may be just what the doctor ordered. Take time to indulge in a treatment with an esthetician, develop a new beauty routine, revisit the gym, and buy yourself some fresh flowers to beautify your home or office.

Things as simple as a new nail polish color, haircut, or new dress will help jumpstart your new dating life: They'll make you feel sexy—and 100% ready to take on any attractive new prospects.

And if you'll be dating online, enlist a good friend (with a great camera) to take some super-flattering photos for your profile—they'll help set you apart from the competition—and best promote your kick-ass online dating profiles.

grab your gal pals

...or guy pals, or whichever friends that are supportive and caring. As the Sex and the City character, Carrie Bradshaw, once said in earnest, “No matter who broke your heart or how long it takes to heal, you’ll never get through it without your friends.” She was right: You need a good support group. Rally the troops for a night of date-hunting; set up get-togethers where you'll inform married friends you're getting back into dating; let all of them know you're open to being set up on blind dates, too. Trustworthy comrades who have your best interests at heart can be your staunchest dating allies.

go exploring

Nothing, yes nada, will happen if you don't put yourself out there. Venture out of your comfort zone and simply explore what life has to offer. You’re never going to meet a thrilling new person if you're hanging around the same old places, doing the same old things.

Try something new by signing up for a sports team, volunteering at a nonprofit, or heading to a new bar. Likewise, if you aren’t that into Tinder, try some different online dating apps by researching and experimenting with those best aligned with your personality and lifestyle.

be yourself

Pretending to be someone you're not will only backfire: Always be yourself, and own who you are. And don’t be tempted to morph into a potential new partner’s perfect person, either. (If you hate smoking and your date asks if it’s okay to light up, be honest and tell them you’re not into it.) Remember that there are, quite literally, millions of fish in the sea. Be true to yourself and your core beliefs.

think positive

Not every person you date will be “the one”—or even worthy of your love. Yes, you'll undoubtedly have some bad dates, but it doesn’t mean you're forever destined to remain single. True love takes time to develop, so if you run into a few bad seeds, remain positive. (Besides, some truly bad first dates make for great stories.) Chin up: Your special someone does exist, and eventually, you'll find who you've been looking for.

Read All About It

If you're ready to get back on that horse, peruse these four books. They're chock-full of sound advice to help you get you back into dating—while enjoying it, too.

On Pursuing Healthy Relationships

A white book cover with black and pink writing entitled,
Henry Cloud Boundaries in Dating $12
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On Bringing Back The Art of The Date

A white book cover with a blue candy heart that reads,
Greg Behrendt and Amiira Ruotola It's Just a F***ing Date $15
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On Dating With Confidence

A blue book with a thought cloud entitled, Dating Again with Courage and Confidence.
Fran Greene Dating Again with Courage & Confidence $4
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On Healing Past Relationship Hurt

An orange book cover with white and black writing entitled, Whole Again.
Jackson MacKenzie Whole Again $10
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