Dating Diary

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Cosmo’s new Dating Diarist, Maggie Kim, 26, is a writer, musician, and self-described serial dater. Dig into the romantic chronicles of a sassy single girl in search of Mr. Right.

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Just broke up with Ben (Virgo, 27). Feel slightly bad but also relieved. Always knew he was too cute to be trusted. In the two months we dated, I wasn’t allowed to break his unspoken rule: Never ask him what he’s up to when I’m not with him. Way too casual for me. We’re history.

Worse, he says he wants to be friends. What the hell does that mean? Am way too confused right now to contemplate such a lukewarm arrangement. Then again, we do have stuff in common — he’s a writer and rocker like me — so maybe friendship would be a better choice than deleting him from my Palm completely. Am supposed to help him paint his apartment this Saturday. Should I? No. Will I? Probably.


Broke down and helped Ben paint. Even went Stationery Supplies and other shopping together for the color (he wanted a pansy pale blue, but I steered him toward a manly forest green). Between coats, we sipped margaritas and flirted up a storm. Then we crashed on the couch to watch a movie, but due to the paint fumes (or could it have been the margaritas?), my pants wound up somewhere around my ankles. Truth is, sex with an ex is so good, I’d almost break up with a guy just to get it. Mega morning-after weirdness, tho. Did brunch together. Very bad idea. Too many unresolved questions. Does this mean we’re back together? Does this mean we’re friends? Should friends swap orgasms? After picking at our egg-white omelettes (w/o once looking into each other’s eyes), we exchanged an awkward kiss on the cheek and bolted.

Micha (my older sis) says that there’s no way I can be just friends with Ben. “Guy/girl platonic relationships end after puberty,” she said over the phone. To prove her point, she asked me if I currently had any male friends, qualified by “You can’t want to sleep with him, he can’t want to sleep with you, and he can’t be gay.” Glimpsed at my Palm and saw mostly men I want to sleep with, men who want to sleep with me, and my best gay friend who thinks that we would make an incredible couple if he were straight. Hmm.

There is Paul (Pisces, 42). He’s definitely just a bud — a strong-jawed, take-no-crap entertainment lawyer I met six months ago at a record-release party held at Studio 54. Hilarious to hang out with but out of my age range. And he’s never laid a hand on me. Micha (aka the supercynic) said, “He’s just taking his time before he makes his move.” I told her she was nuts, and (to prove a point) I called Paul to see when he’s free to meet up.


Micha was right: Paul isn’t a bud. Just found out he falls into the category of men who want to sleep with me. Figured this out the instant he picked me up in his Jaguar convertible and gave me one of those icky hugs that last a millisecond too long. After untangling myself from his arms, I suggested that we catch a flick.

All night, Paul played the perfect gentleman. Opened doors, walked on the outside of the sidewalk, slapped down cash for movie/popcorn/drinks, no q’s asked. Icky hugs aside, I started to get into it. Have to admit, there’s something to be said for older men. Deliberately wore a skin-covering, long-sleeve shirt. Paul mentioned that he liked my other tops better (i.e., the cleavage-baring halters). Wonder if it was a no-holds-barred come-on or a fashion tip? I’ll assume the latter until he tries to cop a feel.


Hallelujah! Just met the cutest, sweetest, smartest, sexiest guy: Jackson (Cancer, 31), a film director/fierce intellectual. Yum! We met over watermelon martinis at Lotus. I was totally mesmerized by his deep voice; he was taken with the eye-catching elephant tattoo on my lower back. We spent the entire night talking and laughing and dancing and kissing. And kissing a ton more. Evening low point: A heel on my green snakeskin stilettos broke off during one of my intoxicated pirouettes. As Jackson dropped me off at my door with a kiss, he gallantly offered to get my shoe fixed. I handed them over because (1) it was his spin that caused the breakage and (2) it’s just the excuse I need to meet up with the intriguing Jackson again.


It’s been 3 days, 10 hours, and 36 minutes, and Jackson hasn’t called. Beginning to let my imagination run wild. Maybe he’s prancing around his apartment with his size-10 feet stuffed into my strappy shoes. Maybe I should give Ben a call to see if he’s up for painting his kitchen maroon.


Finally got an email from Jackson. Wanted to write back in caps “WHAT TOOK YOU SO LONG?” but instead played it cool. Turns out there was a reason for his hiatus. He said he’d lost my contact info (those lethal watermelon martinis) but tracked me down through a friend of a friend. Such determination! Plus, he reassured me that my shoes are currently at the shop, receiving the best repair job money can buy, and that he’ll deliver them in person ASAP. Can’t wait to see him (and taste him) again.

And wouldn’t you know it, I just got a call from Ben offering me some guitar lessons in exchange for my lovely paint job. Gave him a noncommittal maybe. Silently gloated but then felt guilty. Started wondering if it would be fair to jump into bed with other men without telling Ben first. Or should I tell Jackson that I’ve been sleeping with Ben? Or should I just keep my mouth shut and enjoy all the attention I’m getting?


Had band practice tonight. Rehashed my guy probs with the boys. Their opinions about bedding down w/ old flames ran the gamut. Ray (the lead singer) said it’s a great way to fill the gap between serious relationships. “Being single can be frustrating,” he said. “At least you can jump into the sack with a past lover and know the sex will be satisfying.” John (the lead guitarist) begged to differ. “If you have sex with an ex long enough, it morphs back into a relationship,” he said. “Even if you think there are no strings attached and are dating around, you’ll feel guilty. Trust me, it isn’t worth it. Make a clean cut.”

Final tally: Jackson = thumbs-up; Ben = thumbs-down. I love my band. Guess they’re the only real straight male friends I have. Though our new second guitarist is awfully adorable.

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Dating Diary, Seekyt
General Contributor
Janice is a writer from Chicago, IL. She created the "simple living as told by me" newsletter with more than 12,000 subscribers about Living Better and is a founder of Seekyt.