Selecting this year’s Top Singles was no easy task. To be a TCW single, you need to be well-rounded with a sparkling personality and stellar professional/charitable contributions. And it doesn’t hurt if you’re a little easy on the eyes. And in 2014, we found an impressive mix of entrepreneurs, health professionals, media personalities and more. Overall, it’s an eclectic group of good-natured singles that you’d probably either want to date, fix up with your best friend, or if you’re ‘of a certain age,’ introduce to your daughter or son. So have a look and see if anyone piques your interest!
The photographs in this feature were taken by Adrian Orozco and Ashley Fischer at ¡AY CHIWOWA! on Chicago Avenue, at an exclusive party to introduce the single women and men to each other.
Terrence Chappell 28
Social Media/Social Media Project Manager, Walgreens
On the side: Joffrey Auxiliary Board, AIDS Legal Council of Chicago, ChicagoPride.com and Huffington Post.
My Twitter bio reads: I’ll wear my Converses with anything and to anywhere.
Friends say I’m loyal, silly, approachable, a bit ratchet, confident, awkward, fun, all smiles, a secret momma’s boy, helpless romantic, thrill seeker, risk taker and a gentleman.
My life motto is “Make it rain.”
On my day off, you’ll find me in bed watching Netflix and doing some writing.
If I won the lottery, I’d probably just buy a big house for my family and myself to live in together and stock the shelves with an endless supply of Hostess Honey Buns and the freezer with frozen White Castle burgers.
The best day of my life is every day! I’m grateful for each day – past, present and future.
The title of my autobiography would be Outsider.
I can talk for hours about serial killers. I’ve always had a morbid curiosity about their minds and if I weren’t in journalism and social media, I’d probably be a profiler for the FBI.
I couldn’t live without family, friends, laughter, White Castle, baked brie, honey buns, Prosecco, Pandora, Harold’s Chicken, silver foxes, fresh linings, green tea, Jack Black products, and barbeque sauce – all in that order!
If I could travel anywhere in the world, I’d go to Japan. I’ve been practicing Nichiren Buddhism for several years now, so I’d love to go to to meet President Daisaku Ikeda, who is the founder of Sōka Gakkai International (SGI), the international offshoot of Sōka Gakkai, a Nichiren Buddhist – he’s truly an amazing man.
You’d be surprised that I know how to surf! I learned during my summer in Coffs Habour in Australia when I was 18.
My biggest fear is being in the exact same place in life as I was the year before – stagnant. I gotta keep it moving!
I wish I knew at 21 that the real world is an actual world and she ain’t cute sometimes.
In 10 years, I see myself married and traveling the world with my husband.
My best date was when this silver fox took me to Sixteen at Trump for the chef’s blind tasting course and wine paring. It was just so unexpected for a first date, but the conversation was great, he was a good guy and I didn’t have to reach for my wallet.
My ultimate turn-off is delusional arrogance.
My ultimate turn-on is a kind heart.
David Claus 49
Advertising/Creative Director, McGarryBowen
On the side: Stray Animal Advocate.
On my day off, you won’t find me. I’ll be holed up writing or off the map.
My secret talent is ukulele building.
The title of my autobiography would be Defying Darwin.
My biggest fear is not stepping into the face of fear.
Friends say I’m adventurous, funny and nice.
I love my job because it’s different every day.
My life motto is “Expect nothing. Be ready for anything.”
If I won the lottery, I’d find the most impactful way to give it all away.
If I could travel anywhere in the world, I’d go to the lush forests of Berzerkistan.
My ideal partner is remarkably intelligent, adventurous, affectionate and nice to the core.
My favorite date spots are Blackbird and The Hideout.
My ultimate turn-on is just a hint of perfume.
I can talk for hours about martial arts, travel, food, dreams, pets…
On the side: Chicago Youth Centers, After School Matters, Chicago Public Schools, Chicago Urban League and Rainbow Push Coalition.
The great thing about my job is I get to reach people in need, have my ear to the community and work to make a difference for underserved populations.
Friends say I’m honest.
On my day off, you’ll find me listening to Garth Brooks or playing my guitar.
If I won the lottery, I’d donate a good portion to charities supporting children of incarcerated parents, buy a house for my aunt and make sure my nana’s healthcare needs were met.
My best day was the day I realized that I no longer looked to others to feel worthy.
My secret talent is ballet.
The title of my autobiography would be More Than A Conqueror.
I can talk for hours about politics.
I couldn’t live without my smartphone.
If I could travel anywhere in the world, I’d go to Iran.
You’d be surprised that I speak four Middle Eastern languages.
My biggest fear is failure.
Date me because I’m a good listener, fun loving and energetic.
In 10 years, I see myself running for U.S. Senate.
My ideal partner is well-rounded, funny and has a charitable heart.
My best date was a horse and carriage ride after dinner in downtown Chicago.
My favorite date spot is Paris Club.
On the side: Lynn Sage Cancer Research Foundation, Lookingglass Theatre Company, B.I.G. Baseball Academy and University of Chicago Laboratory Schools Alumni Association.
My Twitter bio reads: Just a girl. In the City. Hoops, music, friends, Faith, livin’ the dream…
Friends say I’m loyal, funny, competitive, and always up for trying something new.
On my day off, you’ll find me at the gym, engaging in a little R&R and reading fashion magazines.
If I won the lottery, I’d travel, buy my parents a vacation house and support the many fantastic charities in Chicago.
My secret talent is parallel parking.
I can talk for hours about the NBA.
I couldn’t live without my loving family, hilarious friends, pick-up basketball, Bob Marley’s music and summertime in Chicago.
If I could travel anywhere in the world, I’d go to Greece.
Date me because I can hold up my end of the conversation, know the best places to hang out in the city and at 6’0” I’m easy to find in a crowded room.
In 10 years, I see myself doing big things with great people, enjoying a wonderful life.
My ideal partner is ambitious, funny, social, and likes watching/playing sports. Intellectual curiosity, strong problem-solving skills, and good dental hygiene are required. Kind eyes and an interest in community service are preferred.
My ultimate turn-off is a man who can’t make a move.
My ultimate turn-on is a man who’s confident and thoughtful.
Brian Faga 29
Senior Linux Administrator, Oprah Winfrey Network
Friends say I’m fun, loyal, honest and dependable.
You’d be surprised that I spent a good portion of my childhood living in Australia.
I love my job because media is never boring. There’s always a new puzzle to solve!
My secret talent is playing the harmonica.
On my day off, you’ll find me exploring this great city in which we live or watching a movie. Probably depends on the weather.
If I won the lottery, I’d buy an unnecessary penthouse with a view and more guitars than I can count.
I can talk for hours about food, music, movies and whiskey.
If I could travel anywhere in the world, I’d go to far too many places to mention. Practically? New Zealand or Italy. Impractically? Antarctica.
My biggest fear is spiders.
My ideal partner is someone with whom I can do absolutely nothing with, and have a blast doing it.
My ultimate turn-on is a well-developed sense of goofiness. You can’t take yourself too seriously.
My ultimate turn-off is smoking. A cliché answer but true nonetheless.
Date me because I’m quite chivalrous (frequently to a fault) and a great listener.
Click through the pages for more singles!