First date ideas for over 50s

First date ideas for over 50s

 · 13 min read

Looking for great first date ideas? Thankfully, there are many things you can do on a first date (and probably some you have never thought of!). There are also some tips and tricks for choosing something that suits both you and your date, as well as date nights that can ease things up for shy and quiet people.

  • Learn the difference between a first date with someone you know and with someone you met online
  • Find great ideas for first dates that will relax you and help you create great memories
  • Get ideas for conversation starters as well as questions to keep the conversation engaging
  • Figure out what dates you and your date are most likely to enjoy

First date ideas: FAQs

  • Is dinner a good first date idea?

    If you met someone online and have never met them in person before, then no, it's not. Choose something short and sweet, like going for a coffee. Even better is a takeaway coffee where you go for a stroll together, giving you something to talk about as you see things you can point out as you walk.

    If you know you have a lot to talk about, then, by all means, a dinner date can be nice, if not very unique.

  • Should you meet in public for a first date?

    Unless you know someone before the date, then yes. Definitively meet in public for the first two to three dates

  • Should you dress up for a first date?

    That really depends. Show that you put some care into your looks, but gauge dress code depending on where you are going. You don't want to overdo it. If you're going for a walk in the park, it's different from going for drinks at the Ritz. Dress accordingly. 

  • What are great first date activities?

    It's good to do things together as it stops awkward silences from forming. For example, you can have a laugh while bowling or keep busy during a cooking class. This will also give you things to talk about if you sit down for drinks or dinner after. In this article, you will find a ton of great first date activities.

  • What are the best dating sites for finding new dates?

    If you're looking for dates, look at this article I wrote previously about the best dating sites for over 50s

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Let's have a look at the best first date ideas around, as well as at some great conversation starters so that you and your date have something interesting to talk about!

The difference between a first date and a first meeting 

If you use dating apps, the first meet up with someone isn't what I'd call a first date. You have no idea if there's chemistry or not. It is just as likely to turn into a chat with a friend or a somewhat stilted conversation with someone with whom you have little in common. That's why I always encourage people to meet up as soon as possible to see if there is real-life chemistry. It also stops you from getting attached to an imaginary person who might get in the way of you liking the real person. You might actually miss a great person because you're missing your "ideal" picture that you painted of them while chatting online. 

So, let's first look at great ideas for first dates that are first meetings, not a "proper" date. 

If you're still looking to find a date, check out this article I wrote about the best dating sites for over 50s

The first rule about first meetings

The first rule is to keep it short. If they turn out to be a bore, you don't want to waste your time. On the other hand, if they're fun, you want to leave them wanting more. In addition to that, if you are a bit nervous, keeping it short will lessen the pressure and mean you don't have to keep a conversation going for a long time. 

Telling someone you'd love to meet them for a quick coffee as soon as possible to see if there's chemistry is a great idea when online dating. If you have a yoga class, a meeting, work, or something else to dash off to afterwards, all the better. However, you need to tell your date upfront, so they don't get offended. Frame it up as a quick meeting to gauge chemistry.

The above holds true for blind dates that your friends and family set you up on, too.

Brilliant ideas for first meetings

While grabbing a quick drink or coffee is generally the best starting point, there are a few different ways to go about this. For example, you can:

  • Grab a drink from a coffee shop and go for a stroll in a park
  • Get a drink at a farmer's market or flea market and walk around the market looking at the different stalls
  • If it's the right time of year, grab a mulled wine by a Christmas market or ice skating rink to check out the skaters (or skate yourselves!)
  • Meet in a park for your coffee or lunch break and bring tea/coffee and a sandwich
  • Grab an ice cream or drink by the beach and go for a walk 
  • Choose a pub, bar, or coffee shop that has an interesting theme, menu, or decor, so it gives you ample to talk about during the date

Remember to ask your date what things they enjoy and are comfortable doing. 

Another vital thing to remember is that you should meet in a public place that's relatively busy. That will help keep you safe. If you go for a walk on the beach or in a park, choose a popular one. Don't tell them your home or work address unless you're sure they're legit.

Now let's have a look at proper first dates - the one you arrange once you know you actually want to go on a date with someone. 

Deciding on a first date activity

So, you know you want to go on a date with someone, even if you don't necessarily know exactly how much chemistry there is. You've met them before, though, and you're interested enough to arrange a date. So, now, what should you do?

There's the traditional dinner, or drinks at a nice bar or pub. You can't really get away from that one. However, a dinner means sitting down to talk to someone for an hour or two depending on where you eat and how many courses you have. When there are first date jitters in the air, it might be best to break the tension before you sit down to eat. That way, the conversation will flow better. Plus, a date activity is more memorable than a traditional dinner date. 

If you do something other than dinner, though, it pays to know some of your date's preferences. But, of course, if you don't know them well enough to know if they prefer bowling over a comedy show, you can always suggest three date ideas and let them choose. 

If you are talking with them, ask questions about what kind of dates they enjoy and what interests they have - it will help you come up with suggestions. For example, if they love art, it's easy to take them for a stroll in an art gallery followed by drinks or dinner. If they're crazy about the outdoors, you can go for a hike, or why not try kayaking? Just make sure they can swim and aren't scared of water... 

First date ideas that take place indoors

Let's face it: it often rains in Britain. There are no two ways about it. Meaning that most date nights take place indoors for about eight months of the year. Below you'll find some date night activities that will enable you to have fun, or that are interesting, or simply things that will give you something to talk about if you have drinks afterwards. 

  • Playing ping pong, visiting a bowling alley, or playing pool - given there's an excellent venue near you, not a place that smells like stale beer...
  • Doing an improv class together (make sure they are comfortable with this first!)
  • Attending open mic night at a pub or seeing a theatre performance at a pub (maybe check the quality first - read reviews online)
  • Go to see some live music, whether a small concert or just a band playing at a pub
  • Take a dance class together
  • Do wine tasting or wine pairing (sometimes there are chocolate and wine pairing classes, for example, or wine and cheese pairing classes at local bars)
  • Attend a cooking workshop 
  • Attend a poetry reading, or a book signing by an author you both enjoy 
  • Hit up the trivia night at a classy pub
  • Play video games at the local arcade (pretending it's still the 80s!)
  • Take a pottery class
  • Attend a local theatre performance or movie night with post-performance questions
  • Attend a lecture you'd both enjoy
  • Visit a museum for an exhibit
  • See a comedy show
  • Play board games at a local pub or coffee shop
  • Attend an event at a local coffee shop 
  • Go to karaoke night at a local bar
  • Go to a local bookshop or library and pick out books you think the other person would enjoy, then sit down with a coffee somewhere and do some reading
  • Go for a weekend drive to have brunch at a restaurant in the countryside 
  • Check out the activities at your local sports centre 
  • Have high tea at a classy hotel, department store, or tea shop
  • Try out an escape room 
  • Do anything tourists would have done, but you haven't yet 
  • Visit a nearby castle
  • Google fun date spots near you and see what comes up - try one out if it sounds like fun

Many of these activities can be followed by drinks, tea, or dinner somewhere nearby. Check out what's available beforehand so you can recommend something if you both feel up for it. Remember to plan around what you're doing, though. For example, you won't necessarily want to go for drinks after a show on a Monday night if the show finishes at ten o'clock! 

Outdoor date ideas

Thankfully, it's summer sometimes. And even in spring, autumn, and winter, there are gorgeous days to be had. But, of course, you get different vibes when out and about, so trying to have some outdoor dates is excellent (even if it's the second or third date). 

  • Join a scavenger hunt or do geocaching
  • Go hiking
  • Go rock climbing (with an instructor or group!)
  • Go kayaking or rowing and have a scenic picnic by a lake
  • Go for just the picnic somewhere - you can have one in a park in the city, or head to the countryside for a country walk and picnic (or lunch at the pub). If you fancy, you can bring a bottle of wine and a blanket you can snuggle up on. If you want something unique, bring some poetry to read aloud, or a board game you can both enjoy. Or simply a deck of cards!
  • Go to the local farmer's market and get something to eat
  • Visit a flea market
  • Go ice skating (some rinks are indoors too!)
  • Visit your nearest botanical gardens
  • Go zip lining
  • Go for a walk along a local canal, or river
  • Play tourists in your own town for a day, or in a nearby town, walking around to different destinations, map (or smartphone!) in hand
  • Attend a local festival or event that takes place outdoors (scan local Facebook pages, newspapers, or TimeOut depending on where you're based)
  • Play a round of mini-golf
  • Have a late-night picnic where you do stargazing
  • Go to the train station, pick a train, and head out for a day-long adventure
  • Visit a local farm 
  • Volunteer together at an animal shelter, soup kitchen, or foodbank
  • Do something wild, like going paragliding or axe throwing (yes, it's a thing - maybe people have been binge-watching "Vikings" on Netflix too much...)
  • Enjoy a drive-in cinema experience. As this is pretty intimate, you might want to save it for the second date, but there are plenty of open-air cinemas these days, too

With any of the above, check your date's fitness level first. You will not want to plan a day of walking across London if they are incredibly unfit or hate to walk. Likewise, what you consider a short country walk might be what they think is a long country walk. Any of the above can include a stop for a drink or some food along the way. Remember, it's important you actually have a chance to speak with each other. 

One interesting tidbit of information is that people appear to fall in love more easily if they do activities that release adrenaline. So while sky diving might be a bit extreme, it may not hurt to do some zip-lining if you're both up for it! You can always save it for the second date, though...

Conversation starters

While all the above date activities should give you plenty to talk about, there are other topics that make for great conversation starters. 

  • What's one achievement in your life that you're really proud of or that simply brought you a lot of happiness? 
  • What are your favourite hobbies and spare time activities? (Once they get talking, ask them follow-on questions about what they love about the activities and try to find out more in general.)
  • What are three things you want to experience in life and haven't yet? Or that you wish to experience again? 
  • Did you have a hero growing up?
  • What are some of your favourite books and movies? 
  • What do you enjoy about our town? 
  • What's one holiday you went on that was great and one that was a complete disaster? 
  • What's your favourite childhood memory? 
  • What are some of your favourite places you've visited? 
  • What's one downfall you had that you learned a brilliant lesson from? 
  • Do you have any favourite recipes? 
  • What are some of your pet peeves--things you can't stand in other people? 
  • What makes you feel safe?
  • When you plan a vacation, what are the things that are the most important to you? (This is an excellent question for figuring out some values. Are they budget conscious? Do they need to feel safe, knowing all the details about the place? Do things need to be easy? Do they love an adventure? Do they like to visit places that make them look good, such as the French Riviera?)
  • Do you like spontaneity, or do you prefer to plan? 
  • When you buy a new car or house, do you think of safety, economy, or experience first? What seals the deal for you? (Again, look at their values, as it will help you understand them. You can also check out Sandy Gerber's Emotional Magnets to learn more about peoples' "motivators.")
  • What is one thing outside your comfort zone that you really want to do? (As a follow on question, you can ask if they enjoy stepping outside their comfort zone)
  • If you could have a superpower, what would it be? 
  • What makes you feel safe?
  • What makes you feel loved?
  • What's your best relationship advice?
  • Would you ever consider moving abroad? 
  • What's one thing you'd like to change in your life?
  • Do you embrace change or fear it? 
  • Would you say you're traditional or modern in your approach to life?
  • What are qualities you admire and appreciate in people?
  • What does your ideal weekend look like? 
  • Would you say you're an honest person? If so, do you still indulge in white lies to "spare" people from something or spice up a story? 
  • Do you enjoy your career? Are there any career goals you are still passionate about?

If you want to know the importance of asking good questions, read this article about how asking the right questions can help you fall in love with each other! 

It pays to speak up so that they can hear you during the conversation, smile, look them in the eye, and sit back in a relaxed manner (or lean forward a bit while they're speaking to show you're interested). On the other hand, fidgeting, nervously looking around the room, speaking so low they can't hear you, or crossing both your arms or legs show that you are shut off to the conversation, whether due to nerves or disinterest. 

Another tip is to truly listen to what they have to say. Don't think about your reply. Don't judge what they're saying. Instead, repeat things back to them to ensure you got what they said. Do ask some follow on questions from time to time. Do point out similarities between you when they arise. 

After publishing this article, we got in touch with celebrity dating coach and relationship expert, "The Dating Guru" James Preece, who added: "It's perfectly normal to be a little nervous before a first date. It just shows that you care about the outcome. However, the other person will be feeling the same way. This means there will be moments of awkward silence or you might stumble over your words..and that's absolutely fine.

"The best way to avoid being self-conscious is to focus on making the other person comfortable. If you are conscious of how they are feeling and making them feel special, then there's no time to be self-conscious. People like people who like them, so putting them at ease is going to mean more chance of a second date. You can do this with the odd compliment and being as friendly as possible."

Maria Montgomery
Maria Montgomery
Maria joined Age Group in 2020 and specialises in content around dating and mental wellbeing. She has lived in seven different countries, has an entrepreneurial streak and is the owner of Magique and That Woman Is A Woman Productions. Her blog, Confessions of a Dizzy Blonde, offers her life learnings, sprinkled with a large dose of humour…and sex!