The Single Girl's Guide to Dating Again (and Come Out Winning)

Updated 05/01/19
a woman dressed for a date on the street
Merilyn Smith /Contributor

Getting back in the game after a dating drought can be intimidating, to say the least. Even if it’s only been a few months, it can feel like an eternity. So when you do finally say yes to a first date, your nerves are on high alert with both excitement (Could this be the one?) and fear (How do I act? What do I say? Or not say? What do I wear?). We get it; putting yourself out there is hard. It could result in love, or it could result in rejection. It does take some effort, but if the outcome is an awesome and interesting person to share your life with, the risk of being spurned is worth it, right?

So what are you waiting for? There’s never been a better time to get back into the dating game. Here’s how to do it with confidence and come out winning.

make peace with your past

You won’t be able to start a relationship with someone new if you’re still hung up on the venture capitalist who refused to make time for you. Take the necessary steps to get over your ex. Grieve if you have to. Go on a dating detox. Leave your past in the past. Make peace with it. You’ll be able to look toward your future—and hopefully a better relationship—with a more positive attitude. If you find yourself dwelling on your ex, stop your train of thought and remember the good times you had when you were single.

You could do whatever you wanted.

mojo matters

Confidence is attractive. Do what you need to do to get your mojo back. Flirt with the cute barista, leave your number on a napkin for the beautiful chef who personally stopped by your table, or initiate contact with the tall drink of water you’re lusting over on Hinge. When you’ve got your mojo back, you will feel excited and hopeful at the thought of going out with someone new—and that feeling is important to successful dating.


You won’t feel confident if you feel ugly. Take the time to beautify yourself and your surroundings. Get a new haircut. Buy a new nail polish color. Make an appointment with your esthetician. Get a membership at the kickboxing studio down the street from your apartment. You want to feel sexy and ready to take on any new prospects, so refresh your look. Invest in a new dress to wear on dates. If you plan on experimenting with online dating, ask a friend with a great camera to take some photos of you.

Pick the best ones, and set up the perfect online dating profile.

grab your gal pals

Dating is tough, especially when you inevitably run across a few frogs before finding a prince. You’ll need a good support group in place. As Carrie Bradshaw said, “No matter who broke your heart or how long it takes to heal, you’ll never get through it without your friends.” Rally your gal pals together. Tell your favorite ladies you’re making a point of getting back into dating, and ask them if they will help. Get dressed up and go out on the town for a night of date-hunting with your single girlfriends.

Set up regular get-togethers with your married friends where you give them the 411 on your dating life. Let your A-team know if you’re interested in being set up on a blind date.

go exploring

Ready to find the love of your life? Put yourself out there. Go exploring! Try something new. You’re never going to meet a thrilling new person going to the same old places, doing the same old things. Get out of your comfort zone. Sign up for a sports team, volunteer at a new place, or try a new restaurant. Apply the same mentality to online dating. If you aren’t into Tinder, try a different app. These days, there are tons of apps and websites that are helping people find “the one.” Research them and experiment with the sites that feel right for your personality and lifestyle.

be yourself

When you go on first dates, don’t pretend to be someone you’re not. Be yourself. If you hate smoking and they ask if it’s okay if they go and have a cigarette, tell them you’re not into it. Embrace who you are. Own it. Don’t be tempted to morph into a potential new partner’s perfect woman. There are millions of fish in the sea. If your date is shorter than their profile listed and you can’t imagine a life in flats, move on. Be true to yourself and your beliefs.

think positive

Remember: Not every person you date is “the one” or even worthy of your love. True love takes time to develop, so if you run into a few bad seeds, stay positive. Yes, you will go on some bad dates, but that doesn’t mean you’re never going to find love. Besides, bad dates are good stories! Keep on believing that your special someone exists—because he or she does. Eventually, you will find the right person.

Ready to start dating again? Read our favorites guides for the modern single gal below.

Henry Cloud Boundaries in Dating $10
Greg Behrendt and Amiira Ruotola It's Just a F***ing Date $12
Lisa Winning He Texted $8
Sherry Argov Why Men Love Bitches $13

Related Stories