So, It’s Been a While — How to Start Dating Again

It doesn’t matter if you’re recently divorced, widowed for over ten years, or fresh out of your very first relationship—moving on and starting to date again is no small feat. After all, it can be exciting, overwhelming, daunting, and maybe even a little terrifying to navigate the world of dating.

It doesn’t matter if you’re recently divorced, widowed for over ten years, or fresh out of your very first relationship—moving on and starting to date again is no small feat. After all, it can be exciting, overwhelming, daunting, and maybe even a little terrifying to navigate the world of dating. 

If you’re contemplating getting back out there, you’re probably asking yourself questions like how long should I wait to start dating again? And how do I start dating again after a long time? While the answers to those questions will be different for each person, we’re here to help you figure out how to start dating again, even if it’s been a while. 

Whether it’s been three months or three decades since you were last on the dating scene, don’t fret. Below, we offer some top tips for dating after a divorce, a bad breakup, and even a dry spell. From highlighting some signs you might be ready to date again to reminding you to take it slow, our guide provides all the best advice on how to date again.

Look for Signs You’re Ready to Start Dating Again

When it comes to figuring out how to date again, it’s a good idea to think about why you should start dating post-breakup. While there is no secret key to knowing when you’re ready, you might start noticing signs that it’s time to get back out there. 

For example, maybe you’ve spent time focusing on yourself, and you finally feel whole and complete without your ex. Or perhaps your heart has healed, and you’re actually excited about the prospect of meeting someone new. Better yet, maybe someone has already sparked your interest or caught your eye. Sometimes, little signs like these suggest you might be more ready than you realized. 

That said, recognizing when you’re ready to start dating again is just as important as recognizing when you’re not ready. After all, you’ll want to avoid finding a new partner for the wrong reasons, such as:

  • You want to get revenge on your ex
  • You want to get over your ex
  • You want to prove you’ve “moved on”
  • You have insecurities about being single
  • You think a new partner will solve all your problems
  • You think a new partner will complete you

If you feel like any of those are your driving motivators to date, it’s probably best to hold off and work on healing yourself first. 

Ignore Timelines

Whether you’re healing from a divorce or getting over a fling, you’re probably wondering how long to wait to start dating again. And the truth is, however long feels right for you. There is no magic number. Your friend Cindy might have gotten back in the saddle just three months after divorcing her partner of 10 years, while your brother Joe took three years to date again after his college heartbreak. 

While we don’t recommend making arbitrary deadlines for getting back on the dating scene, it can be helpful to give yourself check-ins dates. For example, one month from now, you might assess your situation and see how you feel about it. Still feel too soon? Mark your calendar for another month or two and do another temperature check. If the idea of dating seems a little less daunting (or revolting!) as the months go by, you may be inching closer to the “right time” to start up again. 

Get a Sneak Peek 

Still not sure if you’re ready to date again? Sometimes it helps to see what’s out there before fully committing. 

For instance, join a dating app or dating website so you can browse potential matches without even having to engage with anyone. Or, go to your friend’s birthday party, volunteer in your community, or join a co-ed sports team—all situations where you can suss out singles sans the pressure of actually dating. Who knows? You just might like what you see!

Think About Your Wants and Needs

Before you dive back into the dating pool, take some time to think about the kind of relationship you want. Are you looking for a fun, carefree summer fling, or are you more interested in something for the long haul? Also, consider what kind of partner and future you picture for yourself. For instance, are marriage and kids part of the equation? Or do you want a child-free life where you can travel the world together at a second’s notice? 

Of course, these factors can change over time, but they can provide a foundation for you and make you more intentional about how you go about finding someone. Furthermore, knowing what you want may help you narrow down where to find it and prevent you from wasting your time in the wrong places.

And if you fast forward to when you meet a potential match, we suggest communicating these wants and needs with them to ensure you’re on the same page. 

Start Slow

Just because you’ve decided to figure out how to start dating again doesn’t mean you need to have ten dates lined up right out of the gates. 

Go at a pace that feels right for you—whether that’s one date in the first month or once a week—to avoid burning yourself out. After all, if you put too much pressure on yourself to find “the one,” you might get discouraged and not want to continue pursuing potential matches. 

Allow Yourself to Take Breaks 

Even if you’re 100% ready and committed to finding a new partner, dating can take a lot out of you. It’s mentally and emotionally (and sometimes even physically!) challenging to put yourself out there and meet someone new. 

If you feel like your battery is drained or you’re simply not having fun, take some pressure off yourself and take a break. At the same time, create boundaries for yourself. Maybe that means only accepting one or two dates a week or blocking out your weekends for your own time. Remember, you want to attract someone when you’re at your best—not when you’re stressed and overwhelmed at the mere thought of going on a date. 

Be Realistic

As much as you’d love to fall in love with the first person you meet, that’s hardly ever the case. Dating takes time, and it’s something you have to be committed to in order to see results. Yes, that means there will be some flops along the way, and you might even get rejected. But that’s all part of it, in the same way that you’ll experience amazing first dates, butterflies in your stomach, and maybe even a steamy goodnight kiss. 

That’s why we encourage you to be realistic about your dating expectations, such as realizing it may take longer than you’d like to find a new mate and that you might experience some bumps along the road. Connecting with someone new probably won’t happen overnight, but it’ll be totally worth it when everything finally comes together. 

Giving yourself permission to date again can bring on a lot of different feelings, from exhilarating excitement to sweaty-palm nervousness. And that’s absolutely normal. After all, dating tends to be a little bit fun and scary at the same time. That said, at the end of the day, dating should be enjoyable. If you’re not having a good time, allow yourself room to take a break, readjust your expectations, and reassess your wants and needs. 

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