Dress by Valentino at Neiman Marcus Credit: Photo by Colleen Durkin; Styling by Agga B. Raya; Props and set by Doug Johnston and Colleen Durkin

Angelica Ross
34, Albany Park

Seeking: marriage-minded man

Occupation: CEO of TransTech Social Enterprises

Her friend says: “Angelica is stunningly gorgeous (a former model), recently launched her own business, and was MSNBC host Melissa Harris-Perry’s first ‘Foot Soldier of the Week’ for 2015.”

What do you do when you’re not working?

Writing and playing music.




Dog lover! I’m coparenting a dog with current roommate.

Dietary restrictions?

None—I eat everything.


No, but open to them.



What’s your idea of the perfect Chicago date?

I love the arts, and I love a man who loves art. A perfect Chicago date would include taking in a show at Steppenwolf Theatre or live music at the Double Door, a decadent dinner at Table Fifty-Two, and ending the night with a decaf coffee.

If you were on Jeopardy!, what anecdote would you share with Alex? Also, would you win?

Trivia has never been my strong suit, but I definitely would not tell Alex about that one time I might have peed on myself right outside my apartment door fumbling for my keys.

What’s your preferred method for surviving a Chicago winter?

Having a hot man to cuddle up with is the preferred method, but I’ve been freezing for the past few winters.

If HBO made a miniseries about your life, who would you cast for the lead role?

Gabrielle Union or Kerry Washington.

Go-to karaoke song?

“More than Words” by Extreme.

What do you find boring?

Environments that lack diversity.

Who would you kill if you could be guaranteed you’d never be caught?

I’m a lover not a fighter, I couldn’t harm a fly.

What was your first e-mail address/AIM name?

I paid someone a lot of money to bury that.

Please describe your understanding of cell-phone etiquette.

Text messages are meant for quick messages, not full conversations. When a guy constantly texts but never calls, it says he’s not serious.

What’s your zombie apocalypse contingency plan?

Don’t need one. I’ve been on this planet a few times before—I’m sure I’ll be back again.

What 2015 ephemera do you think you’ll be nostalgic about in 2035?

#MCM (Man Crush Mondays on Instagram)

What contemporary trend or habit do you detest?

Cultural appropriation. I’m really over white America criticizing black culture for the very things it ends up eventually stealing and making money off of.

Credit: Photo by Colleen Durkin; Styling by Agga B. Raya; Props and set by Doug Johnston and Colleen Durkin

Say you’re going to be interred like an Egyptian pharaoh. Who or what is in your burial chamber with you?

I’m wearing a pair of red-bottom Louboutin shoes and there’s just a letter stating, “I loved my shoes so much that I asked to be buried in them. If you dig me up and steal my shoes I will haunt you, your children, and your children’s children for all of eternity.”

It’s time to decide who gets to board the generation ship that’s evacuating earth for a planet we haven’t yet fucked up beyond repair. Who goes and who stays?

Well, my home girls are coming with me for sure! Janet Mock, Jen Richards, Laverne Cox, Geena Rocero. People who must stay are all people who refuse to respect diversity. If you want to continue to make laws governing other people’s lives, stay your ass on planet earth.

Where would you set the minimum wage?

$15 an hour.

If you could only eat one type of sandwich for the rest of your life what would you pick?

Gotta love a Skippy PB&J—I like it any way you serve it, smooth or crunchy!

What is your favorite curse word?

I must say I love a good use of the F word.

Where were you this past Fourth of July at 7:18 PM?

At home, comforting my dog from the fireworks-induced anxiety attack she was having.

How long do you stay angry, and do you get loud or quiet?

I don’t stay angry long. I see anger as useful, but if it sticks around too long it can be toxic. If I’m angry you might not know it, as I tend to get quiet. But if I’m livid, you will know it.

Do you like to talk about a movie right after you’ve seen it?

Yes! I actually talk about it during­—”Don’t go in there, bitch! Watch out!”

What’s the biggest sacrifice you ever made for someone you care about?

Despite the brutal winter, I lent my car to my family in Wisconsin while I brave the cold on the CTA. I can bear the breeze if it means my family and grandmother are able to get around and stay warm.

If you didn’t have to be yourself, who would you be?

Beyonce. Need I say more?

At what stage in your life were you the best (or worst) version of yourself?

Between the ages of 19 and 21, which is when I began my transition. That was a time when I couldn’t imagine the things I can now take for granted.

Are you afraid of or excited to face the unknown?

I face the unknown head on, with or without fear.

Who is your intellectual idol?

Marianne Williamson. I love her spiritual intellect.

Do you have a personal mantra?

Keep it moving.

What’s your CTA pet peeve?

Manspreading (men sitting on the train with their legs wide open taking away space from those siting next to them).

What’s your favorite cultural depiction of Chicago?

I love the line from Kanye West’s song “Jesus Walks” that says, “You know what the Midwest is? Young and restless.” It just says so much about the hustle of living and working in Chicago.

Do you have any hidden skills or talents?

I hide nothing. I use all my talents. But as far as talents go, I play piano, guitar, and I sing.

So, really, why are you single?

Others say transgender is still so new to everyone; it will take time. But in my experience, that is a lie. Men have always known about us. I am rarely welcomed into a man’s world and offered a chance to get to know him around his friends and family. I’m the girl he’s afraid to bring home to mom. I am unapologetically me—I am bold and I am visible in the media and I focus a lot of my business efforts around economic development in the trans community. I am living on purpose and with purpose, and I have yet to find a man who can see past his fears and fantasies to see a woman worthy of his hand.

Anything else you feel like including to help people get to know you?

Trans women are women nonetheless, and therefore are legitimate partners for men who are interested in women—all the more so if you find authenticity, resilience, and strength attractive.