Strawberry Shake at Lindy's & Gertie's ($4.29)
Between the homemade ice cream and the chunks of fresh strawberries, this is one strawberry shake that can do no wrong. Is it just me, or does the requisite whipped cream topping make the most sense on a strawberry shake? That strawberries and cream combo is such a strong pairing. If you appreciate the ultra-sippable quality of a shake on the thinner end of the spectrum, this is the shake for you.
Birthday Cake Shake at BadHappy Poutine Shop ($5)
If your date is unimpressed by your low key plans, take them to BadHappy and grab a seat at the counter, which everyone knows is the original chef's table. Order a salty mess of a poutine and this shake, which happens to be my personal favorite. This is the ultimate childhood throwback: remember those generic cardboard cartons of vanilla ice cream your family always served with the saccharine grocery store birthday cake? Was that just my family? Anyway, this is the grown-up version of that, complete with crunchy multicolored nonpareils, a genius finishing touch.
Nutella Shake at Edzo's Burger Shop ($4)
You can't go wrong with any of the flavors at Edzo's (and don't forget to check the specials board; the day I went, Salted Caramel and Mexican Chocolate were two of the offerings), but if you have to pick just one to share, the Nutella will not disappoint. If you happen to be blindfolded—hey, I don't know what you have planned for Valentine's Day—there would be no mistaking that chocolate hazelnut flavor, plus you can see actual streams of Nutella running throughout the shake. To bring the romance to the next level, use the shake as a dip for the cheese fries for a twist on that classic Wendy's combo.
Horchata Milkshake at Antique Taco ($4)
Even though this shake is garnished with cinnamon, the predominant flavor is actually banana, so this is an excellent sweet and creamy way to cheer up anyone with the winter blues. Though I preferred foregoing the straw and drinking straight from the cup to get that heady cinnamon fragrance.
Vegan Mint Chocolate Chip Shake at The Brown Sack ($5.50)
If you're date is vegan or maybe just lactose intolerant, take them to The Brown Sack for a veggie sandwich and a mint chocolate chip shake you'd probably never guess is dairy-less. The only hint of soy flavor I detected was in the milky, melted portions of this otherwise too-thick-to-sip shake. The mild mint flavor and substantial chunks of chocolate make it far too easy to polish off an entire mug and a half.
Oreo Shake at Top Notch Beefburgers ($2.90)
Travel back in time to the romantic days of letterman jackets and poodle skirts by sitting at the counter with your date at this real deal, old school diner. Their comfortingly classic Oreo shake is thick enough to hold a spoon upright but somehow just thin enough to be easily sipped during those awkward pauses in conversation on your first date.