Start dating again – no matter what life stage you’re at!

Couple on a date on the beach with a happy dog

There are many reasons why singles might be hesitant to start dating again. Maybe you’re an older single who thinks the dating game has changed too much, maybe you’ve just finished healing after a divorce, maybe you simply feel you’ve been single too long. And, maybe, all you need is a little push to get right back into the dating pool and start swimming once more!

With these top tips, designed for singles at all sorts of life stages, you’ll be ready for new romance in no time. And, if you’re still asking should I start dating again?, our handy quiz will help you know for sure.

Start dating again…find your category!

As an older single
After divorce
After a long time being single
Try our Should I Start Dating Again? quiz

Start dating again as an older single

Your dream doesn’t have an expiration date. Take a deep breath and try again

― KT Witten

If you’re an older single wanting to start dating again, the courting practices of 2019 might seem totally alien. The rise of online dating, and then dating apps, have rewritten the rules of romance. There’s no more waiting three days to call someone after a first date, and no more clear expectations of who asks whom out (or who pays for the date!). Even many of the typical relationship milestones have been redefined.

Yet modern dating also has clear advantages over the way things were. For singles dating after 50 or after 60, making a success of it is all about knowing how to navigate this new landscape:

  • Use an online dating app
    Once upon a time, dating was all about luck: you just had to hope that a) you’d run into someone who was also single and b) that the two of you would be compatible. If you had a niche requirement, like, say, dating as an older single, that luck could be even harder to find. These days, however, it’s so much easier to make your own luck. If you’re thinking about starting to date again, but don’t know where to start, a dating app is a solid bet. The best dating apps can connect you to a wealth of like-minded people, meaning that your problem won’t be finding a date – it will be picking between them!
  • Define your own relationship milestones
    Want to know the cool thing about dating as an older single? You get to redefine what ‘typical’ relationship milestones look like. By the time you’re dating in your fifties or beyond, the questions about having kids or not have been answered, and the lessons you’ve learned from previous relationships have taught you what you do and don’t want from love. If you’re thinking about getting back on the dating scene, know that it’s ok to trust this wisdom. The only milestones you need are those you set for yourself. Maybe you want another marriage, maybe you want companionship – either way, you decide.
  • Don’t take dating too seriously
    Now, we’re not advocating full-blown bacchanalia – that’s the bailiwick of other dating sites and dating apps! But, if you want to start dating again, it is a good idea to not get too serious too soon. Ease yourself back into the pool rather than diving right into the deep end with a serious relationship. If you’re a more mature single who hasn’t dated for a while, try accepting a number of coffee dates before you start thinking about getting exclusive. It will help you get to grips with the way people date in 2019, and give you the insight to know a truly special connection when you find it.

Start dating again after divorce

This is how magic is done. By hurling yourself into the abyss and discovering it’s a feather bed

― Terence McKenna

If you’re thinking about dating after divorce, step one is taking the time to heal. There’s simply no point in dating again if you’re still licking your wounds – rebound relationships rarely last and you’ll find more lasting success if you enter a new romance with an open heart.

Happily, this healing stage doesn’t last forever. There will come a day when you stop thinking about your ex and start wondering what a new relationship might look like – and that’s a great sign that you’re ready to take charge and try divorced dating. Ready to get reminded of just how much fun romance can be? These tips will help you thrive:

  • Don’t let your past define your future
    Dating again after divorce or the end of a long-term relationship? It’s important to know, deep in your very bones, that one failed love story doesn’t doom you forever! Indeed, the fact that your relationship didn’t end the way you imagined can actually be a useful teaching experience that can make you a better partner. Dealing with break-up forces you to learn a whole lot about being strong and independent; not to mention showing you what you need in a relationship (and what you’re able to give). It’s scary to look for love after being hurt, but you have to know that you can find it.
  • Think about meeting singles who’ve been on the same journey
    In the movie It’s Complicated, Meryl Streep’s character is dating as an older, divorced single. She starts seeing Steve Martin’s character and – before one of the sweetest baking montages in cinematic history – their characters bond over their divorces. As a dating strategy goes, it’s not such a bad idea: dating someone who gets it can be a real boon when you’re balancing new love with kids, exes, and all the messy wonder of divorced dating. Happily, such a match shouldn’t be hard to find: the Pew Research Center says 2/5 marriages include at least one spouse who had been married before.1
  • Know your dating boundaries
    One thing to keep in mind when you start dating again after separation or divorce is that it’s important not to repeat old patterns. Don’t just latch on to the first charismatic soul who looks your way after the split: take the time to really think about what led to the end of your last relationship and then set up solid boundaries to ensure that it doesn’t happen again. Bear in mind though – boundaries are not walls. You’re not closing yourself off from meeting someone new; instead, you’re approaching love with wisdom, refusing to accept anything less than a healthy relationship.

Start dating again after a long time being single

To love and be loved is to feel the sun from both sides

― David Viscott

Wondering how to start dating again after being single for a long time? You’re not the only one! This country is full of men and women who’ve had a long period of singledom and are ready for a change but don’t know where to start. But change is possible! It just takes a little push.

Maybe you’ve been out of the game because you’ve been a single parent raising small children, maybe you’re a single professional who’s been focused on work instead of love, maybe it’s just been a while since you met anyone worth dating. Whatever the reason, these tips will help you get out of the rut and right back into dating:

  • Don’t be afraid to go outside of your comfort zone
    If you’ve been single for a while, it can feel pretty safe. You don’t have to share the doona, you don’t have to share the remote, and – perhaps most of all – you don’t have to deal with the fear of romantic failure. The thing is, there are so many more emotions than safe. Yes, love doesn’t always work out, and that can be scary. But when it does work, it’s like the sun coming out after long, grey winter. If you want to replace romantic safety with romantic joy and wonder, you have to get out of your comfort zone and start being proactive about dating again. It’s terrifying – but the rewards are worth it.
  • Find a supportive group of friends (and let yourself be vulnerable)
    Going from single to a couple is far easier when you have a little help from your friends. It’s even better if you can create a singles’ support network: get a few of your single mates together a few times a month and have a cathartic session of commiserating over bad dates and cheering on good ones. To really make this work, you’ll need to open up and be vulnerable – it’s no easy task, but the rewards are manifold. And, remembering how to let people in emotionally is fantastic training for your next relationship.
  • Get proactive about finding love
    Ready to get back into dating? The best way to change your single status is getting proactive about looking for love. After all, unless you’re starring in a romcom, it’s unlikely that love will just happen to you: you have to go out and seek it! If you’re feeling a bit rusty about the whole dating thing, one of the best ways to get going is with a supportive dating site that allows personality based matchmaking. Not only will the people on such a site be serious about looking for love, the matching side of things means that those you meet are likely to be in tune with you: ideal if you want to start dating again!

Try our Should I Start Dating Again? quiz!

It is a risk to love.
What if it doesn’t work out?
Ah, but what if it does?

― Peter McWilliams

Taken these tips about dating again on board and now wondering whether you’re ready for a relationship? We’ve prepared a quiz that can help you decide for sure

Ready to start dating again? Let EliteSingles help you find someone amazing!


1 Pew Research Centre, November 2014 (

About the author: Sophie Watson

See more articles written by Sophie Watson