How to Date Someone Twice Your Age


Meet on Omegle after wading through suicidal Midwestern tweens and Europeans aching to practice their English on you. Introduce yourself with something quirky to emphasize your uniqueness in a world where relationships end with the click of a “Disconnect” button. Carefully exchange vague personal details like location and age. Make sure he lives at least 3,000 miles away so that any chance of a real friendship and/ or relationship is effectively stifled by distance. When he says he is 42, do not express surprise at your age difference. Take it in stride, as if all of your friends began as 40-year-old Internet strangers.

After listening to him talk about his childhood traumas, feel comfortable enough to send a link to your blog. Discuss literature, movies and art. When he mentions the first time he ever went to a concert, quickly do the calculations in your head—you were negative 11 years old.

Let him call your writing beautiful, and let yourself feel good about him calling your writing beautiful. After enough time passes, send him a picture of yourself. Act coy when he compliments you; demure with practiced grace. Let him call you beautiful, and let yourself feel good about him calling you beautiful. After hours of conversing on Omegle, exchange e-mail addresses. Transition to Gchat, the most fertile of conversation platforms, so that your romance can blossom.

Immediately embark upon a long, torrid Gchat affair. Skip local social gatherings so that you can sit in your bed in your small Manhattan apartment and Gchat with a 42-year-old Dutch dude who you swear understands you better than anyone on this planet. Encourage him to figure out how to operate his webcam so that you can video chat, but again, he’s 42, so of course it takes forever. When he finally figures it out, act like you just wanted him to hook it up to say “hi.” Abstain from showing him any of your body parts on video chat for like, at least a month.

Learn how to say, “I want to fuck you” and “I really like you” in Dutch. Deploy them at moments that make him lose his breath. You are young so everything you do and say, every angle you twist your body, is somehow sexy to him. Revel in this. Let it comfort something gaping in you, something you can’t explain.

After six months, explode with joy when he announces he has booked a plane ticket to New York. On a hot June day, don your prettiest sundress and meet him at the Starbucks near his hotel in Chelsea. Hug him awkwardly, your arms flung like wet noodles around his neck. He is so tall in person!

After dinner, invite him back to your apartment and tentatively kiss. Assuage his worries about your age gap by putting your hand on his dick. In the middle of making out, get so worked up that you spill Grolsch on your $2,000 Macbook. Ignore it and get back to lockin’ lips—you will learn later that Apple warranties do not cover sex-induced-alcohol-spills.

Go with him to touristy places all over Manhattan, like Battery City and Central Park and the Empire State Building. Abandon your negative attitude about tourist traps simply because you love spending time with him, even if it’s in Midtown. In all events predating 2000, defer to his cultivated wisdom. Feel close to him by claiming you are an old soul, already world weary at 21. Eat Thai food and drink beer and watch the Kentucky Derby on a bar TV in the West Village.

Avoid any and all serious conversation about the future—your future—until the last night you are together. In bed, initiate weighty discussions about What This All Means. He is twice your age and does not want kids and oh yeah, he lives 3,000 miles away. Avoid actually resolving these issues by having sex again. Afterwards, make puppy dog eyes and brandish the brightness of your youth like a weapon. It is a razor-sharp diamond, a silvery throwing star. Launch it at him right between the eyes, and miss.

On his last day, have him drop you off in a cab on your East Village stoop. Cry when he puts his rough hands on your shoulders. When he says, “Go get ‘em, tiger,” feel like you just ended an affair with your high school lacrosse coach.

After he leaves, send drunk, rambly e-mails about how much you miss him. Tell your friends you are in love with him and convince yourself you mean it. Cry so much on video chat that you actually make him cry. Fantasize about dropping out of school and moving to the Netherlands and tending to plants in a window flower box. Feel startlingly satisfied with this plan.

Let him break it off because you’re in too deep to do it yourself. Everything is against you: the age difference, the distance, the cultural chasm. Know that it’s the right decision, but write angsty missives about heartbreak anyway. Logic is one thing but emotions are another: in a fit of raging loneliness, adopt a cat from the ASPCA. Spend the rest of the summer mourning, and rebound in the Fall. You’ve learned your lesson this time; your new boyfriend is only 10 years older.

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