ating is stressful no matter how old you are. The benefit of dating in your 40s and 50s is you probably already know what you want and deserve in a relationship and are less likely to waste your time dating people you don’t thoroughly enjoy. A study in Psychology Today found that people who stayed single for longer became more satisfied with their lives. These tips will help you limit the stress and intimidation of dating. Let’s talk about:

  • Where to meet people
  • Date ideas
  • Important dating conversations
Two men in their 40s enjoy a date at a vineyard.
Dating in your 40s and 50s means you already know what you enjoy--find someone who likes the same things and do them together!

Where to Meet People to Date in Your 40s and 50s

Meeting People to Date in Your 40s and 50s 

There are lots of options for where to meet people in your 40s and 50s. Some of these ideas involve getting out of your comfort zone and being willing to take chances, but some fit right in with your daily schedule! 


If you meet someone at your job you automatically already have something in common, but you risk still having to see them everyday if your dates don’t go well. Volunteering allows you to start with something in common without the pressure of dating a coworker. If you’re not sure where to start, explore the volunteer opportunities near you and find something you’d like to do.  

Meeting someone while volunteering for a cause you care about means you also know that the person has similar values and interests. A recurring volunteer event makes it easy to see and talk to a person more than once before making an official date which makes the stakes lower. Plan to attend the same volunteer events together or show up hoping to run into them and see if they’re looking for you too!

Places You Already Go

Think about where you like to go on a day off or a sunny weekend--your favorite restaurant, coffee shop, bakery, park, movie theater, store, or wherever else you enjoy spending time. Next time you’re there look around and see who else is there. Although it might seem stressful to walk up to a stranger and start a conversation you will probably feel more comfortable in a place you know well. 

If you start seeing the same person at your go to coffee shop over and over then you have a conversation starter. Talking to someone about where you are and what you’re doing then you don’t have to figure out if they’re single and interested before you speak to them. These locations are also neutral meeting places where you both go anyway, so why not go together and see what happens?

Places You’ve Never Been

You know that bungee jumping trip or pottery class you’ve always wanted to take but none of your friends want to do? Now is the time! Don’t be afraid to do things on your own because it’s a great way to meet new people and you get to do something you like at the same time. If you don’t already have your own list of new things to try, consider these options:

  • Classes - Maybe you don’t want to go back to homework and paying tuition, but there are plenty of fun options for classes out there. You can find classes for art, cooking, writing, gardening, and so much more. You can meet someone while learning a new skill.
  • Clubs - Join a book club, running club, bird watching club, chess club, or any other group that sounds fun to you. In groups like these you can do something you love with a bunch of other people who love it too, which is a great way to meet someone. 
  • Restaurants and Bars - If you’re tired of the people you tend to see at your usual spots, trying a new restaurant or bar can introduce you to a new group of people. Take yourself out to the spot that has been intriguing you and see who you meet there.
  • Trips - Not everyone can fly to another country, but even heading to the next town over can be a great opportunity to meet new people. Plan a road trip or a day trip to a new place--you can easily start conversations with strangers by asking for local recommendations or tips. 


Although online dating can seem strange and you may not think you’re ready, keep it in mind as an option. You can take part in this modern form of dating from the comfort of your couch. Sort through the options for online dating and see if it’s a good choice for you. 

Former Relationships

Although no one recommends dwelling on an ex, in your 40s and 50s you can reflect on past relationships and see if any of your former partners are worth revisiting. If a relationship ended because you and your ex partner were in different places in life or wanted different things, those obstacles may not be in the way anymore. 

If you’ve stayed in touch with any former partners who are still single there might still be a connection there that you haven’t thought about in a while. With someone you’ve already dated you know what to expect and what you liked and disliked about dating them before. You can enter into a new, more mature version of a past relationship. Be careful to avoid falling into a rut with an old relationship not getting what you want out of dating in your 40s and 50s. 

A group of friends in their 40s share a meal together.
Bringing your date to events and meals with your other friends can take some of the pressure off. 

Date Ideas

How to Not Stress about Dates in Your 40s and 50s

Dating would be a lot easier if you didn’t have to spend so much time figuring out what to do for a date. Where do you want to go to eat? What movie do you want to see? Do you want to go for a walk or a bike ride? No one wants to make a decision that the other person doesn’t like so you end up stuck with no plans. It’s good to have some reliable date ideas in your back pocket to avoid dates that stall out before they even happen.

Use Your Home Turf

If you pick a place you already like then you take some of the guesswork out of the date. You’ll stress less if you already know where to park, what the wait time is like, when it’s crowded, or what’s on the menu. 

Your date will also appreciate it if you have a suggestion ready when you’re making plans. With a place you already know you get to show your date something you enjoy which is great for getting to know each other. Once you’ve gone on a few dates you can choose new spots to try, but why not start with a known entity at first to make it easier?

Include Friends

Going out with multiple couples or a group of friends can sometimes be much easier than one on one. If you’re worried about what you’ll talk about the whole time, bring some other people to join in on the conversations. There’s nothing wrong with making sure your date gets along with your friends too.

Find an Event

An event is easy to use as a date that has been fully planned for you. Your options will depend on the time of year, but there’s almost always something going on. There are lots of websites and apps that list events happening near you. Look for: 

  • Food Festivals
  • Concerts 
  • Plays or Dance Performances
  • Craft Fairs or Sidewalk Sales
  • Museum Exhibits
  • Speakers

Choosing an event to attend together can help you discover more similar interests and attending it gives you something to do and talk about that someone else planned. 

A couple in their 40s and 50s hug their dog.
It’s a good idea to make sure your partner fits in with your lifestyle. 

Important Dating Conversations

Topics that Matter for Dating in Your 40s and 50s

These probably aren’t things you need to bring up on your first few dates, but before you get serious with someone you should make sure you’re both on the same page for a few key things. Remember to add anything else that is important to you to this list--you know what matters to you and your relationship. 


Dating in your 40s and 50s means it’s possible that you, your partner, or both have been divorced or have had long term relationships without having been married. The point is that people might have solidly established feelings about marriage before they start dating. Whether you would really like to get married or have decided marriage is not for you, this is something you and your partner should discuss at some point in your relationship. 


If you or your partner has or wants kids this is a very important topic to cover. It’s not fair to you or your children to bring someone into your lives that isn’t going to be invested in the family--on the other hand getting involved with someone’s family is a huge responsibility that shouldn’t be taken lightly. You and your partner should have a serious conversation about any present or possible future children.

The Past

You very well might have some baggage left over from dating in your teens, 20s, and 30s that won’t just disappear in your 40s and 50s. You and your partner can save yourselves some time and unnecessary pain if you discuss what you’ve learned and are taking with you into this new relationship. 

If you’re just meeting this person now, they haven’t heard any of your stories--good or bad. Fill each other in on what has happened in your lives both to get to know each other better and to help make your future together a happy one. 

Two people in their 50s sit together on a hiking date.
Dating in your 40s and 50s is a chance to meet new people and have new experiences. 

Dating in your 40s and 50s can be very rewarding and will likely be the best dating of your life. Take everything you’ve learned in past relationships and find someone who makes you happy and enjoys the same things you do. For more dating advice, check out some other articles on The Adultist.

Jun 8, 2020

Related Posts

View All