8 tech companies that prove being single on Valentine's Day is actually awesome

Sam Dewey

Being single rocks. Especially on Valentine’s day.

Hear me out — snuggle-wuggling with your loved one after a successful date night on the big day is fine and all, but the whole charade is incredibly inconvenient. You’ve got to buy flowers and chocolates and cards and gifts — not because you want to, but because you’re obligated to. On top of that, there’s ever-mounting competition to be more creative and more romantic than whatever Instagram pictures your plans will inevitably be pitted against. It's expensive, it's exhausting, and it's excruciating. 

I'll take spending the day as a lone bachelor over all of that any day. 

There’s a litany of reasons why being single on Valentine’s Day is actually pretty awesome. Here are but a few, come to life thanks to some of our favorite local tech companies: 

Scoring a table at an exclusive restaurant is cool, but shotgunning a whole pizza Liz Lemon-style is better. The thing about comfort food is that it’s always comfy. Always. And particularly more comfortable than dressing up, waiting two hours for a table, and picking at small plates only to pretend you’re too full for desert.


We’ve all had to feign surprise and delight at a gift that just really missed the mark. But on Valentine’s Day, getting a gift you don’t like can be an especially depressing reminder that your significant other still can’t seem to pass your litmus taste test. With Luxury Garage Sale, we single folk can buy something we're sure to love. After all, no one knows you better than you. 


Everyone loves a good daisy, whether it’s a holiday or not. There's no need to wait for someone else to bust out a vase or two. Just ask Flowers For Dreams, a delivery service for floral arrangements that serves Chicago year round. Take advantage of any sales (perhaps the day after?) to bring some life back into your apartment. Odds are you need the company.


Single, dating, married, divorced — when it comes to relationship status, wine is an unbiased and supportive option for all. It also doesn’t discriminate by day of the week or time of the year, so in its eyes, the fact you’re using Winestyr to order some off-the-shelf Pinot Noir to drink alone this Valentine’s Day is just a happy, serendipitous accident.


Arts and crafts are rad, but they’re not exactly collaborative. For those of us spending this Valentine's Day alone, that's a total non-issue. While going to a BYOB painting class with a date is probably fun, using Blitsy to order some adult coloring book to augment your Scandal-watching me-time is pretty preferable, indeed.


Dare we say couples massages are overrated? It can be just as fun (and ultimately, effective) to go with a friend. Or a neighbor. Or a stranger. Or alone. You do you, Chicago. Whatever you choose, Whittl — a Chicago-based company that makes online bookings (for everything from massages to nail appointments) easier and faster — has got you covered.


Anyone who says paying money to watch a formulaic romantic comedy is a better investment than learning how to forge a sword, how to write calligraphy, or how to parkour across the city is lying to themselves. With Chicago-based Dabble, you can look for classes to spend your Sunday working on the most important person in your life: you.


Dating is expensive, and not just on Valentine’s Day. If your lack of romance has lead to a couple stray bucks, you’ve actually got a couple of options. And no one knows options better than dough. This Valentine’s day, check out how dough’s software is making it easier for traders — veteran and novice alike — to trade options.

Images via Shutterstock. 

Have a tip for us or know of a company that deserves coverage? Shoot us an email or follow us on Twitter @BuiltInChicago.

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