Drinking alone is one of my favorite pastimes. I know what you’re thinking, Negative Nancy, but some of us enjoy an evening sans company. Valentine’s Day is nigh, so for you single folk who have never allowed yourselves to indulge in solo drinking, let me offer a (totally ridiculous) guide. Treat it like a date and follow the rules: no crying, creeping or yelling at people. Go ahead and have a heart-shaped pizza delivered to your house if it doesn’t go well—or even if it does.
Make a reservation. Setting a specific date and time says you’re serious. But don’t get embarrassed when the host asks how many. Just say, “I couldn’t possibly sum up the many versions of myself with a number, but if I must, two please.” Yes, two. You’ll want to spare any strangers from getting too close. Your night is about to get weird.
Buy yourself a round of shots. Dates are nerve-racking, and there’s no shame in having a shot (or five) every time you get nervous or insecure about sitting alone. It’s not like you’re keeping up with anyone but yourself. Heck, go crazy, get a shot-ski for one.
Order your friends. If you get bored, just remember you’re never alone with the whiskey list. There, you’ll find an endless lineup of new friends on demand. Just open the menu, pick your preferred age and behold name after name of whiskey daddies past: George Dickel, Ezra Brooks, Evan Williams or maybe even Old Grand-Dad if you’re lucky. Some are cheaper and harsher than others, and most are men (fortunately or unfortunately). If whiskey is an established enemy, peep the beer menu. You might find a Matilda, Lolita or Rosa depending on the season. You’ve got options.
Take a selfie. Position yourself under the moodiest lighting in the bar and snap a grainy pic that really captures how sexy and confident you feel to be out on your own. Caption accordingly and post to all forms of social media with #selfie #solodate #treatyoself #metime #ihatevalentinesday #dontneednoman #unlessyouwannadate #DMme. Do this before you get too drunk to avoid wasting your entire date on your phone reassuring your friends that your mental state is fine and that time you got wine-drunk listening to Thom Yorke and dangled your leg out the window of your highrise apartment building was a one-time deal.
Slide your hand up and down your own thigh suggestively. This night is all about you, babe. You deserve to feel a little sexy. When both hands aren’t occupied double-fisting that shot-and-beer special you ordered, give yourself a little thigh love. And be sure to avoid eye contact with anyone else in the bar. You wouldn’t want them to think this is about them. And speaking of eyes, are yours glassy yet? No? Good, let’s keep this date rolling.
Play drinking games. When you’re drinking alone, every cup is a solo cup. Games always make for great date conversation, especially when the bartender is beginning to think you’re deranged with all that muttering going on. Give Tear Pong a whirl. Here are the rules: Order an assortment of shots. Set them up in a pyramid across from you at the table you reserved for yourself. Write the names of all of your failed Tinder dates on cocktail napkins and ball them up. Proceed to toss said napkins into the shot glasses, drowning each in alcohol, not unlike your sorrows, hopes and dreams. Even if you miss, take all the shots.
Split the check with yourself. Remember, you’re still on a date. Putting the tab on one card and offering to “get the next one at the next bar” doesn’t send the same message as cutting it right down the middle. Insisting on an even split says, “I’m a respectable human who can hold her or his own” without giving the impression that you’re out to take advantage of yourself. You always did find your independence sexy, right?
Go home. I bet your mom told you not to [bleep] on the first date. Well, she’s right, so before you get any ideas about chatting up that cutie at the end of the bar with your insufferable bourbon babble, think about your mom. No, you may not go to another bar—this is a date, not a pub crawl. Order yourself a Lyft (don’t be that person on the CTA), and remember what I told you about getting that little heart-shaped pizza order ready. Ah yes, home is sounding much better, isn’t it? You can kiss yourself now.