Valentine's Day Date Ideas

Hello Lovely,

Valentine’s Day is totally overrated, but there are still some hopeless romantics out there looking to keep the spark alive. At this point, I’m sure everyone is tired of the traditional dinner and movie date, and let’s face it, taking your girl to a club is just no longer cool. Step your game up! So I’ve rounded up 5 really fun and creative date ideas for anyone looking to shower their loved one with affection on this special day!



A romantic Cuddle Kit is an amazing gift for your anniversary, your spouse’s birthday, Valentine’s Day, Christmas, OR just because! It would also make a cute wedding or bridal shower gift, or a quick-pick-me-up for a cold weather day. It can be thrown together in a jiffy, and who wouldn’t LOVE a night of cuddlin’, snugglin’, and lovin’ in a basket? It’s quick, easy, AND romantic, plus, it comes with a darling, free printable gift tags and “Snuggle Up” banner to help you have the most romantic cuddle around. Doesn’t get much better than that!

Here are some suggestions of what you might put inside…

  • A soft, fuzzy blanket

  • Some Bubbly

  • Chocolate Truffles

  • A lovey, dovey movie

  • Some Candles

  • Some Romantic Music

  • Socks

  • Hershey Kisses

  • Cocoa

The opportunities are literally endless! Just include whatever you think is comfy, cozy, and super cuddly.


Romantic Rooftop Date

Meeting and falling in love is such a thrilling, exciting time! Enter the romantic rooftop date-perfect for a picnic!!  And why stop at a picnic blanket when you could have a table and chairs?! Don’t have a flat roof?  Are you living in an apartment without roof access?  Well, don’t let that stop you!  Ask to borrow a friend’s roof for the night.   (I’m pretty sure it’s empty and available.)  Or look for a place in town with access to a great view.

Even if you are solo, all of these activities are fun things to do with your friends and family during the cooler fall and winter months. Give them a try and report back!


Sign Up for a Cooking Class

When cooking isn't your strong suit (and restaurant reservations are booked to the max), sign up for a last minute cooking class where you can learn to make each other's favourite meals. Things always tend to heat up in the kitchen.

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A Wine Bar Crawl

Instead of sticking to just one spot, hop from place-to-place and order different kinds of wine and tapas along the way. It's waaay more interesting than a boring ol' sit-down dinner. Of course, it doesn't hurt stashing one away for later too.

A Scavenger Hunt

This Valentine’s Day, add a little family fun with this Valentine’s Day Scavenger Hunt that everyone can enjoy! You can make up your own, complete with creative challenges, photo missions, and sexy prizes. I’ve even got two ideas for you. The first is specific to Valentine’s Day and only requires your significant other. Not only is this scavenger hunt easy to set up with a cute bag label you can print directly onto the bag, its full of fun activities that will create a memorable Valentine’s Day adventure. Follow all of the scavenger hunt clues to reveal hours of Valentine’s Day fun!

The second option is something I did four years ago for a significant other’s birthday. Just invite your most adventurous friends, print off the clues and let the race begin!

Do you have another fun Valentin’es Day date idea? Sound off below!

Friday Favourites: Cool Date Ideas for Valentine's Day

Hello Lovely,

Valentine's Day is soon upon us (only 11 days) and if you're in a relationship, you're probably trying to figure out what to do on this special day. Some people go all out while some just want to forget the day exist. No matter where you fall on the spectrum, we here at Life By Olivia have got you covered for the best date ideas. Whether you're married, dating or long distance, we've got you covered! 

Simply download our guide below, schedule some time with your partner and go over which date ideas sound ideal to you. It's on a 1-3 scale, with 1 meaning, "Nah I'll pass on that idea" and 3 meaning, "Yeah, I'd love to do that". It's a great way to learn more about what interests your partner while finding new ways to connect with them!

Which date idea are you most excited about? Personally I can't wait to try the online karaoke with my beau. This is prove if he really does like my singing or not :). Tell us which date idea you like best. And if you're flying solo this year, feel free to try any of these ideas with your best friend!

WednesDate: Fun With Charades

Hello Lovely,

Undoubtedly a party favourite has to be charades! It's a great way to show how in sync you and your significant other are, and if you're not, it's still a good way to learn new things about them! But when you're apart from your beau, it could be hard to share fun moments together over board games. If board games are your thing, Fun with charades is a website that lets you play charades with friends online with your webcams! It’s like having a party without having to leave your seat.

Pictionary online games have always lacked that special something that real life charades offered, but now you can make a total fool of yourself on cam. Invite your friends to a room, or play with others online. Act out word clues over live online video. No registration is required!

Wednesdate: Saturday Morning Cartoons

Remember the "good ol days" as a kid where you would wake up early every Saturday morning to watch your favourite shows? How about a trip down memory lane? However, unlike your childhood, in this date you two can both sleep in as most of these shows from back then are now on the web! Get comfy, watch them together and reminisce about your favourite 'toons!

My boyfriend and I grew up in the 90s cartoons era. Even though he's older than me so he watched the 80s cartoons too, he loves the 90s cartoons more, so this date was a no brainer for us!

 What You Need

  • Breakfast Foods 
  • Pyjamas 
  • A list of your favourite cartoons 

 Step one: Set the time. Set up a day and time to have this silly date. It doesn’t necessarily have to be on a Saturday morning. It doesn’t have to be in the morning at all. It simply needs to be a time when you two can ideally meet together without distractions (we hope).

Step two: A taste of Nostalgia. Be sure to wear pyjamas, or anything else that makes you feel snuggly and comfortable. Bring your favourite cereal or other breakfast food and drink to the party. Additionally, both of you can write a list of all the cartoons you used to watch as a kid and plan to watch as many as you can together.

Step three: Watch Together! Hook up and connect your webcams and watch your favourite cartoons together while enjoying a wholesome and delicious breakfast. Go down the list you made together and see how many cartoons you both used to watch, or discover new cartoons you’ve never seen before. It’s a blast from the past with the one you love!


Tips and pointers!

Try watching some older cartoons, like Popeye and Betty Boop, or older versions of the Looney

Toons! Try your beau’s favourite breakfast cereal (or meal) instead of your own to see how you like it.



Have you ever won one of those cereal box prizes? What was your favourite part about Saturdays as a kid besides cartoons? What was a typical Saturday for you then versus now? What do you miss most about being a kid? What did you like to do when you were a child? Do you remember anything about your personality when a child? What did you like about school? Describe the first memory you have of going to school. What were your favourite cartoons and TV shows? What didn't you like about school? What was your favourite toy? Do you still have it?



Every last Wednesday of the month, we will feature a short & sweet long distance relationship date kit. Each “WednesDate” will include a free full length video and or other online or printable activities to accompany it.

If you’d like to be notified about our “WednesDates” each week, Subscribe to our newsletter & you’ll get them delivered straight to your inbox!

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Free Wine Tasting

Tuscany Wine and Olive Oil Tasting!

 March 17th

      6pm - 8pm     

At Young's Fine Wine Boutique!
Make it a date night and be the first to take advantage of these beautiful olive oils from 5 different regions, paired with delectable wines from Tuscany, Italy! See you there!

All wines, champagne and liquors will be 10% off the night of the event!
Tel: 601-0021
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Olde Town Sandyport(across from Twisted Lime & Post Office)
The Young's Fine Wine Team
Will, Laura, Kyle, Stefon, Niko, Marco