Shannon

Gregory

Amanda

Jerod

Darnell

George

Ashley

Keith

Brieauna

Cuffing season is upon us. That’s why so many Black millennials are looking to trade in the party life for cuddling with bae on chilly nights. However, the season’s quest for love isn’t as easy as the moniker suggests. So The TRiiBE put out a call for some fly and introspective Black singles in Chicago to discuss the highs and lows of dating in today’s digital world. Click the gifs above to learn more about each millennial, and then click the questions below to read what they have to say.

I’ve lived in New York, Washington DC and Atlanta, and dating is a little tough there. People are much more focused on being single and more focused on their careers. So you have people in their late 30s who are single and proud. That’s kind of the norm. I’ve only been here [in Chicago] for two years and people are much more focused on relationships. People are more focused on dating. They want to get married. It’s a priority to them.
— Amanda
It’s hard. It’s really hard. I want to date someone who moves in the same communities and circles as me. I wanna be with someone who I can take to the Black and Brown Babes Brunch and someone who’s going to be like, ‘Let’s go check out that protest together.’ So when you limit yourself that way, it’s even harder. [Also], I’m pretty successful in my career for my age. That intimidates a lot of people. A lot of dudes will be like, ‘I work at a pizza shop.’ And then I tell them what I do and they’re like, ‘Nevermind. You’re a real adult.’ I’m not an adult. I just have a cool job.
– Ashley
To be honest, I don’t think Chicago’s gay scene is that much different than the heterosexual scene. You have so many different guys out here that are hustlers and finessers, and you have to try to decipher or weed out the bad ones. So it’s kind of hard. As far as dating or living in Boystown, it’s more caucasian there than Black. [Overall], Chicago is a pretty accepting city. I’ve seen guys lay on each other on the train. I haven’t been in any parts where people looked at me funny or anything
– Keith
It’s hard because everybody knows everybody in some way, some how. You always get the, ‘you look familiar’ or ‘i heard about you’ story. I don’t even know what that means. I don’t know if that’s a good thing or a bad thing.
– Darnell
Hard! I’ve tried dating apps. I have to scroll through, like, 15 people to find one Black person. It’s a lot of work and I get frustrated with the apps. I tried dating naturally but I haven’t been very successful at that.
– Shannon
Very sporadic. I tend to go with the flow because every time I’ve tried to – for lack of better words- ‘try too hard,’ I find the wrong people.
– Brieauna
Maturity. In my early 20s, I wasn’t really dating. I was being with a person, understanding what their favorite color is and their favorite song. – George
In high school, I always attracted the ratchets. Then you get to college and start being around people who are more on your level. I started attracting more sophisticated women. – Darnell
When I was a teenager, I really didn’t know how to talk to a woman or a lady. Now, the more dating I do, the more [I focus on] meaningful conversation. I get to break down who the person is instead of getting straight to sex. – Gregory “DJ Royal”
I have more respect for women because I have a daughter now. That changed my whole perspective. When I was young, I saw it as a sport with women because that’s how the men we grew up around taught us. As I got older, I started to realize women are probably the best friends you can have in a relationship. They’re not trying to hurt you or steal from you. Also, I would see the shit my mother would go through with men. That ain’t cool. So my perspective changed and continues to change every day. – Jerod
In high school, I dated whoever was around. I would go to parties and concerts and whoever I met, and thought was cute, was who I would date. In college, I didn’t really date that much because I had a long-term boyfriend. I had this boyfriend who lived in Illinois, and I lived in Massachusetts, so I got to do whatever I wanted. When I moved to Chicago five years ago, we broke up and that’s when I got into internet dating. I hate it. I hate OKCupid and Tinder. There are so many trash people. You’ll see one person in that trash who, in any other circumstance would be mediocre, but you’re literally just like, ‘Well, this guy didn’t send me a dick pic so I guess I can message him back.’ – Ashley
When I was younger, I was adamant about getting in a relationship or having a boyfriend. Now, I need substance. I don’t care about a relationship. I need you to bring something to the table because now I’m looking for a future. In my world, It’s hard for a guy to go up to another guy and talk. So we utilize things like Grindr, a dating app for gays. Although it’s 2017 and we are much more accepting of gay or homosexual behavior, it’s still taboo. We have to be, not necessarily hush-hush, but very discrete in how we approach somebody. – Keith
When I lived on the East Coast, I met a lot more people in person. Here [in Chicago], I meet a lot more people online and on dating apps. On the East Coast, men are much more aggressive and they’ll just approach you. – Amanda
“I’m more so one of those people who give all my time and effort once I’m fully invested. Through the years, I’ve learned not to necessarily hold back but to have my reserves, and not give it all up on the first go ’round. – Brieauna
Some of us are dating for a life partner. Some of us are dating to fuck. Some of us are dating to have fun. I’m looking for a friend. As I’m getting older, I want to date and find that friend who I can just look at one day and be like, ‘I really love this person,’ even if they get on my nerves or I get on their nerves as much as they get on mine
– George
I look for compatibility. Someone who can vibe off of me and I can vibe off of her. Someone who I can [argue] with but, at the same time, we understand and respect each other.
– Darnell
Trust, honesty and consistency. I don’t like [women who are] too clingy physically but clingy mentally.
– Gregory “DJ Royal”
I am looking for a man of great character. A man who is ambitious, smart and funny. It’s important to me that he’s a kind and supportive partner. He [should] have a good relationship with his family or, if he doesn’t, he’s looking to improve his relationship with his family.
– Amanda
Honesty. Strength. She has to be spiritual and God fearing. That’s first and foremost because I know we can build from there. Family-oriented, and can cook. We can’t eat out all of the time. My mom can cook so you gotta be able to cook.
– Jerod
I look for someone who has the same drive and ambition as me. Someone who’s really curious. I like to go to a lot of events. I might not go to the club every night, but if you’ll go to a panel talk with me or go to a TV screening or movie screening, I’m into that. I just look for people who aren’t afraid of new experiences.
– Ashley
Loyalty is a big thing for me. I also appreciate someone who is crazy about me. I don’t want a guy who’s going to next me. I want a guy who’s going to fight for me.
– Keith
I’m looking for someone who’s ready to do fun and crazy and different things with me. I’m not one of those people who wants to stay at home all the time.
– Brieauna
I look for someone who matches what I bring to the table. I look for somebody who is ambitious, intelligent, kind and respectful, funny and attractive.
– Shannon
Turn ons are understanding, consistency and curiosity. If a person can put me on to new music, I love that. I love swapping songs with people and I love a foodie.
– George
Turn offs are being loud, obnoxious and crazy. A turn on is someone who can dress. If you can catch my eye off what you got on, that’s fly.
– Darnell
I don’t like grumpy men. I don’t like men with negative attitudes. I don’t like men who aren’t self starters because I have a day job and I run several other companies. So I need someone who is gonna take charge and step into that role and help make decisions on my behalf. I’m turned on by innovation. I like men who are really creative. Guys complain about women using them to go on dates. But, a date doesn’t mean a ton of money. If you take some time and invest energy into doing something creative, you can have an amazing free day.
– Amanda
Facial hair is a turn on. If you’re at the same concert as me, that’s a turn on. People who watch the same TV shows as me, because I write TV reviews, that’s a turn on. I hate people who are super cocky. So many guys in Chicago are like, ‘Oh. I went to Whitney Young and I’m so cool.’ So you wear a suit everyday. I don’t care.
– Ashley
A turn off is lowkey competitiveness. Don’t try to compare yourself to me because we’re supposed to be one. We’re supposed to combine and help each other, not fight each other over who does what. Patience is a fucking turn on. Being you is a huge turn on. Walking around the house with your hair nappy and not concerned about makeup. Being silly is a turn on. We can joke. We can laugh. Then, I know I have a best friend and not just a girl I’m dating
– Jerod
Nice teeth and clean fingernails are turn ons. I consider myself to be somewhat of a dresser. Do I wear designer labels? No. But, you need to be able to compliment me. That turns me on. Intelligence turns me on. The ability to hold a conversation, and not just about sex but something political, that turns me on. Fuck my mind, so to speak.
– Keith
Smells are big turn ons and turn offs for me. People who are very self-centered is a turn off for me. I’m one of those people who are very caring and open to my friends. So, if you’re one of those, ‘I’ve got to make sure I’m good’ people, that’s a turn off.
– Brieauna
Honestly, the biggest challenge is myself. I need to learn when to step back and analyze a situation. Think logically and not emotionally. I definitely make mistakes and put myself in situations where I’ve acted out emotionally instead of stepping back and thinking logically. – George
I think it’s more of me wanting too much or not enough, if that makes sense. Another challenge is finding someone who understands my busy schedule but, at the same time, still wants to put up with me. – Darnell
Keeping the interest there. I feel like it starts off hot and exciting. Everybody is all into it, and then everything dies down after three or four months. I haven’t really had something that was very long and thriving. – Brieauna
I don’t know if it’s a Chicago thing, but I haven’t really found people who are serious about dating. For them, it’s more of a, ‘let’s hook up,’ thing. – Brieauna
I find that I attract men who treat me really well but they may not be that interesting. They don’t have any aspirations of stepping outside of their comfort zone. I’m not in the business of trying to change people. I think you should accept people for who they are. But meeting someone who can teach me something, grow with me and explore the world with me, that’s ideal. – Amanda
[Dating] apps make it feel like, ‘I can meet a better person tomorrow.’ When we date, nobody really knows what they want right now. You’ll meet someone and be like, ‘Oh. We click. Cool.’ And maybe, before the age of Tinder, you would try it out and get to know each other longer. Now it’s, ‘I saw that we have 20 mutual friends on Facebook. You dated three other girls that I know. I know this and that about you. I could probably find someone else on Tinder in three hours. So let’s just call it a wrap. – Ashley
My biggest challenge while dating would have to be consistency. People fall back so quick. So my fall back game is amazing, too. It’s sad because I almost go into something anticipating the fall back. I anticipate in three or four days, I’m going to be talking to someone else. – Keith
I love music so going to a concert and enjoying each other’s company could be super lit. Then, leaving time to talk to each other afterwards since you can’t really talk in a concert.
– Shannon
An ideal date night for me would be dinner and a movie, but at my place. Wine. Just chilling and talking shit. Something that’s really relaxed so we can both be comfortable and be able to let loose and give our best selves to one another.
– Keith
A local date might be us taking our cameras and going on a photoshoot where we go shoot in the park. I think that would be a lot of fun. In my romantic wildest dreams, we would go to dinner. We hit it off and we fly to another country and go to a soccer game. I want to fly to Barcelona and then go to a Euro match.
– Amanda
For an ideal date night, we’d meet at Cole’s in Logan Square. That’s my favorite bar. Hang out there, or go to a concert, like a DIY show. Then, probably go for late-night weird walk around town in a new neighborhood or just checking out some abandoned buildings. And drinking while we do it.
– Ashley
Let me give you a dope scenario. At home. We’re chilling. I have a chef come through. We’ve got the rose petals everywhere. You don’t have to wait to get home if you want to do your thing. You’re there already. The music is playing and it’s intimate. We can have discussions because there’s nobody around to censor us. Massages afterwards. I love movies. We can analyze movies. Then, we make love and fall asleep. Wake up and do it again.
– Jerod

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