How to Hook Up with the Coolest Boy from High School Now That He’s Kind of Fat

Lady Boner Kill

For years you stared across the cafeteria at the coolest guy in school, quietly accepting that you weren’t hot or popular enough to date him. Well, you’re not in high school anymore: You have a job, a Weight Watchers membership, and no hymen. Since he continued his binge-drinking into adulthood, he’s gained just enough weight that this long awaited hookup might be doable. Here are some tips to help you on your petty journey of redemption:


Ask to try on his letterman jacket and falsely claim he still looks great in it. Stroke that ego and let him enjoy his denial. He gets to remember the best time of his life, and you get one step closer to fulfilling your 16-year-old-self’s bucket list.


Get someone else from high school to hit on you in front of him. The coolest guy from high school won’t be able to give up his alpha-male status to someone that knew him in his prime. So like you always dreamed of doing in high school, pay one of the lesser members of his clique to hang out with you at the local bar for a night. He’ll feel compelled to leap into your conversation and pull rank by quoting his favorite lines from Adam Sandler movies. This is a good sign.


Bring up his high school sweetheart to make him open up. It’s common knowledge that he peaked when his long-term high school girlfriend got recruited by an upscale breastaurant and left town. By strategically mentioning her name, you can get him to a tender emotional place and remind him he hasn’t gotten laid in a while.



Give him a dose of tough love. All that acting out he did in high school wasn’t a result of competent parenting. Get upset and yell a little, telling him he won’t amount to anything. Anything that reminds him of his alcoholic mother or his football coach will send him right into your arms.


Announce that you are an adult female willing to have intercourse with him. If nothing else works, try this oldie but goodie: Simply verbally communicate your DTFness. It’s quick, direct, and if he says no, the whole story seems so bizarre most people won’t believe it happened.


Sure, most guys from high school have much better jobs and personalities than this guy now, but you owe this conquest to past you. She would be so stoked right now. Good luck, and remember to use 1,000 condoms.


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