Ambiance Matchmaking Meet Attractive Singles
Ambiance Matchmaking Meet Attractive Singles

Your Complete Guide To Valentine's Day 2020

Holidays, birthdays, and Valentine’s Day can be a confusing time for daters. One may have high expectations for an extravagant weekend getaway, while the other may not feel inclined to celebrate a “Hallmark Holiday.”

Every relationship is unique, with its own set of needs and expectations.

First and foremost, you need to know what are your partner’s needs and expectations. Ask: Do you enjoy celebrating Valentine’s Day? What would your perfect Valentine’s Day look like? How does this sound :::insert plan here::: ?

Communication is key; and in order to get to know your partner, you have to ask questions. Plus, it will help you plan a Valentine’s Day suited to both your needs. Every couple is different, and you should always do what feels right to you, and your partner.

One reader tells us how he and his wife celebrate the day after Valentine’s Day, and call it Serendipity Day:

“Instead of celebrating a Hallmark Holiday, we celebrate the day I said I love you to the woman with whom I had so many serendipity moments. We call it Serendipity Day and because it is right after Valentine's Day, we don't have any trouble getting reservations! We spend the day either going to museums or art galleries, or renting a nice Airbnb in the big city.”

We love this. It shows an effort in creating their own special holiday, and it allows them to celebrate their relationship on this one day.

Not every couple will have their own holiday, and that’s okay too!

Valentine’s Day can be your day to celebrate your relationship, and you can still make it unique. The dating experts here at Ambiance Matchmaking have compiled a list of creative things to do on Valentine’s Day to point you in the right direction.

These date ideas are meant for couples who opt-out of the normal dinner date routine and are looking for a more creative and fun way to spend the day.

Do you and your partner have a unique Valentine’s Day routine? Write us an email and let us know!

Valentine’s Dates: Our Top 12


Anyone can make a reservation at a fancy restaurant, but cooking dinner takes skill. We recommend cooking together if it’s something you and your date both enjoy. Nothing brings people together like cooking and sharing a meal. Decide what to cook and buy the ingredients before your date arrives. And, don't forget the wine!

BONUS: Cards Against Humanity is a great post-dinner game. It's a fun way to get to know things about your date that you wouldn't normally think to ask. Most of the questions can be ridiculous so you can have a good laugh.


Grab a blanket, marshmallows, graham crackers, chocolate, and make s’mores over the bonfire. If you’re lucky enough to live close to the beach (and it’s legal), even better. Getting outside of the house, and cuddling up next to a fire, is low-key but still damn romantic. This can also be a great post-dinner activity.

Ice Skating

If you have a beautiful ice skating rink in your city, like Chicago’s Maggie Daley Park Skating Ribbon, grab your skates and do a couple laps! It’s a great way to get in some exercise, get close to your date to make sure she doesn’t fall, and end the date with some hard-earned hot toddy’s or mulled wine.

Museum/Art Gallery

See what your local museum or art gallery is offering for Valentine’s Day. You may hit the jack pot if there’s a special tour or event, which normally is accompanied with champagne and snacks. If there isn’t anything happening, hit one up anyway and bring your own champagne and snacks, though you may have to wait to pop the bubbly’s until you leave the premises:)

Comedy Show

Your local comedy club is sure to have a special themed night for Valentine’s Day. What better way to spend the whole night than laughing? Laughing and generally goofing off is one of the most rewarding things you can do together. It’s proven to bring couples closer, and it’s FUN!

Brewery Tour

Pick a local brewery and signup for a tour. You get to learn how your favorite local brews are made, and taste each one along the way. Many breweries offer food, so you can enjoy a dinner together while comparing favorite brews.

Wine & Tapas Crawl

Plan a wine and tapas crawl where you try food and wine from different restaurants! Here's how to do it: pick a neighborhood that’s full of great restaurants or pubs, choose five or six that you want to try, and split an appetizer and glass of wine at each one. It’s way more interesting and fun than sitting down at one restaurant the whole night!

(Blind) Wine Tasting

The perfect date for wine lovers! Such a great way to enjoy a variety of tastes, compare wines, educate your palette, and have fun with your date. If you’re lucky enough to live close to a vineyard, see if you can setup a tasting at dusk. What’s more romantic than sipping wine while watching the sunset? Another idea is to host your own (blind) wine tasting. Choose a theme for your wines, setup the blind tastings, have your date try to identify each wine, then switch turns! You can even add an extra element of disguise by blindfolding your date with a scarf.

Spa/Mud Bath House

Your girlfriend will love you for this one! Plan a couples day at a spa or mud bath house. Hey, guys need a day to treat themselves too. Most spas offer packages, especially around Valentine’s Day, that include a sauna, massage, facial, manicure/pedicure, mud baths, and more.

Bike Tour

Rent bikes and tour your city together! Is there an area that you’ve been wanting to check out, or a new bike path? Head out and explore together. Bring a picnic for extra bonus points!

Live Music

Check your local clubs and bars to see if there’s any live music happening. A lot of venues will have jazz, classical, contemporary, and late-night jam sessions. Our Chicago favorite is The Green Mill, a swanky cocktail bar that frequently features Spanish guitarists and swing gitan.

Rent A Cool Airbnb

This is one of our favorites. There are so many cool places you can find on Airbnb. Cabins, lofts, treehouses, boats, castles, art galleries, farms, you name it! Check-in as early as possible (normally between 12-2pm) to get a full day’s worth of exploring the area and living a different life for one day! You can also checkout Airbnb’s Experiences to see if there’s any cool events going on in the area.

Use Valentine’s Day as a catapult to grow in your relationship every day of the year…

To me personally, Valentine's Day is a concocted holiday that forces couples to come together and share their appreciation for one another.

I use to put so much expectation into this one day, where I hoped to walk into a room full of flowers, chocolates, and heart-shaped balloons. I have come to see, however, that the affection for your partner should be shown year-round, in the small daily moments that comprise our lives.

Instead of thinking of Valentine's Day as a once-per-year opportunity, use it as a catapult to grow in your relationship every day of the year. Here are our top 5 ideas to point you in the right direction.

Top 5 Ways To Grow In Your Relationship Year-Round

Take a Moment

Take a moment on Valentine's Day to each say one thing that you really appreciate about your relationship, and one thing that you'd like to work on this year. Relationships are work, but they are a lot easier when you both are on the same page, and communication is the way to get there.

Create a Ritual

Create a daily ritual that will bring you two together. It doesn't have to be anything extensive. Maybe it's a glass of wine in the evening, a cup of tea, or cooking dinner together. Whatever it is, make sure it's an activity with a beginning and an end to signify this is your time to connect.

Make a Bet

This is a fun one. Think of an area in your life you'd like to improve. Maybe you both want to exercise daily, or want to stop drinking alcohol. My boyfriend and I just made a bet that we wouldn't drink for one month. If one of us breaks the bet, that person has to put $10 in a jar. At the end of the month, we'll use that money to do something fun together.

Set a Date Night

Set a date night once or twice a month. This is an opportunity to get dressed up and go out together. Once we settle into our relationships, it's easy to hang out in sweatpants on the couch every night, but it's important to continue wanting to impress your partner. This means making an effort to look good and plan a special activity.


Have one day (Sunday normally works best) when you disconnect from electronics. Put your computers and phones in a drawer, and plan a day on the beach, in nature, or something active you both enjoy. Notice how you feel at the end of the day…

Whether you’re dating, or in a serious relationship, these habits can help improve and maintain your connection. Yes, relationships are work, but no one said the work has to be boring:) If you ever have any questions, contact us. We're always here to help!

Now, let’s talk Valentine’s Day gift ideas…

Do you and your partner enjoy giving gifts? What kind of gifts does your partner like? If you’re not sure, ask! “Do you like exchanging gifts on Valentine’s Day? What kind of gifts do you like?”

Communication is key.

Try to personalize your gift idea as much as possible. Personalization goes a lot further than the price tag. For example, if you know a book she's been wanting to read, buy it for her. If you know a dessert he loves, bake it for him. If you're still unsure of what kind of gift your partner may like, don't fret, it's the thought that counts.

Top 12 Valentine’s Day Gifts For Him

Homemade Dessert

Know your guy’s favorite dessert? Bake it for him! It really is true that a way to a man’s heart is through his stomach.


If he’s a big music lover, there’s nothing better than getting music as a gift. If he owns a record player, buy him a record. If he’s into Spotify, create a personalized playlist for him. For example, I created a cycling playlist on Spotify for my boyfriend because he didn’t have any music for his long weekend bike rides.


I recently had to purchase a nice bottle of liquor for a good friend of mine who likes whisky and scotch. Therefore, I asked every single one of my guy friends which brands were their favorite. Here is the list I compiled: Buffalo Trace, Four Roses, Bookers, Woodford Reserve, Makers, Glenlevit 12, Macallan 18, Johnny Walker Black, Gold Label, FEW (Chicago distillery), Laphroig.

Beer Membership

I bought a three month membership from Beer Of The Month Club for a good friend of mine. They delivered right to his doorstep with a variety of his favorites. All you have to do is choose how many months, his favorite type (lager, ales, stouts and porters, amber, etc etc), enter his address, and make your payment! You can also just purchase one month.


If you know what kind of cologne he likes, this is always a nice gift, and you receive the benefit of being able to smell it all the time:)

Cuban Cigar

A nice cuban cigar is great, if he's into that sort of thing.

Personalized Flask

A nice flask is a great gift for liquor lovers. If you can find a flask that reminds you of him, even better. If you know of a place that will personalize the flask by engraving his initials, bonus points! Remember, personalization is always key:)

Restaurant Certificate

Is there a restaurant you both have been wanting to check out? Write your own gift certificate or buy one from the restaurant of your choice. It doesn’t need to be used on Valentine’s Day, you can use it to create a date night in the future.

A New Book

If he’s a bookworm, buying him something to expand his reading horizons is a great choice. Head to your local book shop and make the rounds. Does he like fiction, non-fiction, mystery, memoir, suspense? Choose a book from his favorite genre, or choose one of your favorites to let him know what you’re into! Another option is to purchase a month subscription from Book of the Month.

Bifold Wallet

Have you noticed his receipts and cash falling out of his old, worn wallet? It might be time to upgrade to a new one. Check out this simple and classic bifold wallet.

Beard Oil

Are you dating a beard guy? Head to Khiel’s and choose from their amazing grooming products for men, including beard oil and after-shave gel.

Classic T-shirt

You can’t go wrong with a classic crew cut t-shirt (grey, white, or navy blue) from J Crew. And you know he needs it.

Want more ideas? Check out goop’s gift guide for men.

Top 12 Valentine’s Day Gifts For Her

Recipe Book

If she loves to cook, head to your local book shop (or online) and find a recipe book full of her cuisine! Even better, if you know she wants to travel to a country, find a culinary book full of recipes from that region.


Buy her a really nice bottle of her favorite varietal. You can also purchase a subscription to a wine of the month club online, and they will ship her different bottles based on her taste. Try Firstleaf Wine Club.

Local Bakery Cupcakes

Buy a box of four cupcakes from a local baker. It's nice knowing they came from a local baker and not a generic grocery store. Get a variety of flavors!


Don't underestimate the power of a big bouquet of flowers. Seriously. It immediately brightens my day every time. Get her favorites, or if in doubt, get a big bouquet of red roses. A classic.


Music lovers LOVE MUSIC. If she owns a record player, buy her a classic record. If she’s more a Spotify gal, curate a playlist based on her favorite bands, new bands she should check out, or songs that remind you of her. Be creative!

A New Book

If she likes to read, buy her a book from your local book shop. Choose a book based on her favorite genre, or show her your world by buying her your favorite book.

Scented Cream

Khiel’s and L'Occitane en Provence both sell excellent body butter and hand creams in gift sets.


I would suggest only buying perfume if you know which kind she likes. Perfume can be a very personal choice for a girl 🙂

Aromatherapy (Scented Oils)

A gift set of natural oils is a nice gift. If you already know which scents she likes, craft your own gift set of two or three bottles.

Spa Day

Treat her to an afternoon at a nice spa! Most spas offer packages including a combination of a massage, facial, and manicure/pedicure.


When it comes to women and gifts, flowers and jewelry go a long way. Do you know what kind of style she has? You can try this classic pearl necklace. What girl doesn’t love pearls?

Goop Gift

Gwyneth Paltrow’s lifestyle brand has a variety of excellent gift ideas for the wellness junkie, the traveler, the host, or the cook. Take your pick, it’s hard to go wrong with any of these options curated by women for women.

Bonus Gift For The More Serious Dater

Diamonds can get pricey, so I recommend this gift for the more serious dater. Check out these beauties.

Don’t forget to check our Pinterest jammed packed with more gift and style ideas!

Taylor Wade

Taylor is one of the founders of Ambiance Matchmaking. She now dedicates her time to curating content for our community through her podcast and blog. Writing and podcasting is the art of great story-telling. As a relationship writer and editor, she has always sought to capture the reality of the dating experience, full of drama, friction, and joy. The best mind is an open mind, so she specializes in asking questions and approaching a story without preconceptions.

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