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How to Start Dating Again After a Breakup, Divorce, or Dry Spell

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Jessica EstradaJanuary 23, 2020

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Whether you’ve been off the market for a few weeks, months, years, or decades, getting back out there is no easy feat, especially if you’re not confident about how to start dating again. Common sense might urge you to be vulnerable, open yourself up for possible rejection, and be okay with the notion of kissing a few frogs in the process of finding a compatible partner. Sound intimidating? No problem if so, because it can be intimidating.

The mere thought of going out on a date after a rough breakup, divorce, or extra-long dry spell might induce feelings of anxiety. Because, for one, where do you even start? Sign up for a dating app? Hire a matchmaker? Slide into people’s DMs? Theoretically, any of those strategies could work, but to help you feel extra-confident in your intention to learn how to start dating again, a few experts share their advice below. Keep reading to snag their top tips for getting back out there, once and for all.

Your 12-step guide for how to start dating again

Photo: Getty Images/South_Agency

1. Close the previous chapter

Perhaps it should go without saying, but before you return to the dating pool, you need to be over your previous relationship so you can officially close that chapter in your life. Without taking this prerequisite step to finding new connections, you run the risk of either getting stuck in the past or bringing that emotional baggage with you on your dates.

“Turn the page, move on to the next chapter,” says Tammy Shaklee, relationship expert and LGBTQ+ matchmaker of H4M Matchmaking. “There is more to the story: Your long life is a series of chapters, with some more joyful than others and some more tragic. But keep turning the page and grow based on what you have experienced and learned.”

2. Tap back into what you love to do

When you’ve been in a relationship for a long time, it’s likely that you may have disconnected, at least in some sense, what you personally love doing with what you enjoy doing as a couple. That’s why Shaklee recommends reconnecting with yourself and writing out a list of what brings you, and you first, joy. Maybe it’s riding a bike, going to the farmers’ market, cooking a new recipe for dinner, or something else. Not only will this practice help you come up with fun date ideas, but it can also help you identify common interests you may have with potential partners.

3. Focus on self-love

Before considering how to start dating again, focus on finding self-love, because you can’t love another person without first and foremost loving yourself. “Love who you are today,” Shaklee says. “Cherish your tenacity on your journey. Celebrate who you have become through the many chapters you have experienced in life. Remind yourself that you are an eligible single.”

4. Get clarity on your needs

Starting to date before you’ve gotten clear on what you’re looking for in a partner is like driving around without knowing where you’re going. Before you go out on your first date, relationship coach Laurel House recommends getting clear on your nonnegotioable needs in a partner and a relationship. To that point, she notes that there’s a big difference between needs and wants: “Needs are what you actually need, or else the relationship will fail,” she says. These may include feeling safe, sexy, and seen, and able to participate in two-way communication. Wants, such as physical characteristics, for example, are like the cherry on top; they’re nice, but they’re not a required part of the foundation of the relationship.

5. Take your time before getting out there—but not too much time

Rushing into dating again before you’re truly ready is not a recipe for success, House says. You may still be holding on to negative emotions from your past relationship which may come across on your dates with potential mates. So don’t be afraid to take your time with getting back out there. That said, don’t wait too long. Not feeling ready yet can quickly just become an excuse that holds you back from your romantic future and destiny. “Some of us feel lonely in our box, but we get so comfortable that we are afraid to leave it,” she says. So, give yourself a deadline and do your best to stick with it.

6. when the timeline ends, access how you’re feeling

That is there to say, is there a timeframe to know when to get back out there? Like, a definitive science to how long to wait before you date again ? Not necessarily. The only guideline you should use is that it’s when you feel your ready, not when anyone else says so. Yes, that includes your friends, your family, the Instagram post announcing your ex has moved on, and so on.

“Knowing when you’re ready to date again is an inside job, and only you have that barometer,” says relationship expert Susan Winter. “Jumping in too soon could have a disastrous effect upon your new found stability. Feeling weak, needy or lonely is a recipe for disaster. Any mate pulled into your sphere at this time is coming in on the wrong frequency, and will end up making you feel like a victim of your own needs.”

7. Recognize a lack of fear when it comes to dating

So again, how do you know that you’re ready? When the idea of sitting across from a stranger and asking how many siblings they have doesn’t horrify you.

“You’ll feel emotionally ready to date when you’re no longer scared of exploring romantic possibilities,” Winter says. “Resiliency is key to emotional survival. Your sense of curiosity must be greater than your sense of risk. This is a luxury only afforded by the emotionally stable.”

8. TheN Give yourself permission to start dating again

So you’ve healed from your breakup and stepped up your self-love quotient—now what? House suggests giving yourself permission to start dating again. To do this, get out a real piece of paper, and write yourself a permission slip to go out on dates. This may sound very simple and even silly, but oftentimes, people feel they need to wait for something external or a sign to green-light their choices. In actuality, though, all they really need is to decide for themselves.

9. Throw the dating rules out the window

If it’s been a heady amount of time since you last dated, don’t feel like you need to catch up on all the current dating rules. “Don’t do what you think you should,” House says. “Instead, do what feels good and right to you.” Let your intuition guide the way.

10. Keep the conversation light at the beginning

Divulging your entire life story on the first date? Perhaps not the best idea of all time. Shaklee suggests keeping the conversation on the first few dates focused on lighthearted topics and to wait until the fourth date to share about more serious things. “You do not want to scare off the other person by sharing too much (or asking too much) too soon,” she says.

11. Try all the different ways of meeting people

If you’re serious about learning how to start dating again, House recommends not leaving things up to chance and using every possible avenue to meet new people. Try dating apps, in-person meet-up groups, working with a matchmaker, signing up for a class that interests you, or even making yourself available to connect with someone while you’re in line at the grocery store. And use your personal network, too. Don’t be afraid to be vulnerable and let your outer-circle friends know that you’re single in case they know of anyone.

12. Pace yourself

Dating is a not a sprint to cross some finish line. It’s a process. It takes time to first find the right person, and then get to know them. That’s why Shaklee recommends finding joy in the process rather than trying to rush it. “Even if it ends up not being a romantic or love connection, perhaps you will meet a new buddy,” she says.

When it comes to putting yourself back on the market, it’s like climbing a staircase slow and steady versus taking an elevator to the top of unfinished floor. And yes, that feels exhausting. But the crux of the plan is to really allow the previous chapter to close, then create a cocoon of self-love. Within that cocoon, listen to your heart and try to recognize when you’re ready to date again. After that, give yourself the permission to get out there with a little patience. You got this.

Originally published on January 23, 2020. Updated on March 13, 2020.

Another dating conundrum: Is it possible you’re with the right person even if you have doubts? And, here’s how to change your attachment style to overcome certain relationship issues.

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