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Home · Relationships

The Relationship Roller Coaster

Many of us have had a mix of wonderful and WTH? moments on our quest for lasting love. A few brave women share the most common (and sometimes crazy!) highs and lows along the ride. Buckle up...
The Relationship Roller Coaster
Andrew Derni/Getty Images
By Charreah K. Jackson · Updated October 27, 2020

Many of us have had a mix of wonderful and WTH? moments on our quest for lasting love. A few brave women share the most common (and sometimes crazy!) highs and lows along the ride. Buckle up…

1. Giving online dating a try.

Charlise Ferguson, ESSENCE.com Partnerships Editor: “At the start of 2014 I decided to check out online dating, something I had frowned on for years. Over the course of three months I joined four sites: OkCupid, Match, Grouper and Tinder. I was not prepared for the madness that would ensue: The first guy lied about his height—he was an inch taller than me, and I’m 5 feet 2. Then there was the nice but boring White guy who revamped his profile after our coffee date. (He went from enjoying ‘history’ to not being able to live without ‘any movie with Kevin Hart in it.’) Next I caught a catfish, a British bloke posing as a sexy import living in Brooklyn. Thanks to what I learned from watching MTV, I did a reverse Google image search and discovered the chiseled arms in his picture belonged to a famous Brazilian athlete! The drama was all worth it when I signed up for Tinder and matched with the director of my favorite indie film, a scientist from Madrid and an art director from Chicago. I think I’ll stick with this app for a while.”

2. Dating a man who wants to be a rapper

Loni Love, Comedian and Cohost of Fox’s The Real: “Being on the West Coast during the rap boom meant that many of the guys I met in my twenties and thirties told me, ‘I want to be a rapper.’ Each wannabe was sure he was going to be the next Ice Cube. They had tracks and little home studios with a couple of computers. One guy I dated worked at the post office and rapped about ZIP codes. I tried to be supportive, but it’s like, Dude, it ain’t going to happen. We parted ways. He is still at the post office rapping.” 

3. Finding out you are the other woman

Jackée Harry, Actress: “I was in a gospel play a few years ago and felt I had met my soul mate. He was witty and in the process of a divorce, or so he said. We started a relationship that continued after the play ended, a show business no-no. Two years into dating, I flew to see him. Downstairs in the hotel lobby, I was shocked to see he had brought his four sons who wanted to meet me, sons he never mentioned before. I then got a call from his wife on my phone saying she was missing out on the fun. He had given her my number and we all ended up back at their house. She served us dinner. Instead of poisoning me as I had feared, she asked for my autograph. Later that night she started to tell me about the trouble in their relationship, as if I were a relationship counselor. I got out of there as quickly as I could.”

4. Realizing you are dating a weirdo

Monique Kelley, Creator of Confessionsofaserialdaterinla.com: I was dating a cool but rather large guy. I put my vanity aside when he invited me to one of L.A.’s best steak houses. The conversation was going great until he said ‘You have to experience The Golden Rod of Power.’ I choked on my wine once I finally realized what he meant. ‘Are you trying to pee on someone?’ I asked. He replied, ‘I don’t have to pee on you. It can be the other way.’ I suddenly lost interest in my sauvignon blanc. I threw my napkin down and walked out.”

5. Getting your heart broken…

Recovering Romantic: “Four months before my wedding, my then fiancé and I shared our photos in ESSENCE.com’s ‘Just Engaged’ feature. One month before the big day, I found e-mails from his lover revealing their affair. It was as if my entire world had stopped. But if I was honest with myself, I had caught glimpses of the man I was going to marry, such as the unanswered phone calls at night he claimed were from his boys and the makeup on his shirt. I was just too busy picking out peonies to see it. And now I had a wedding to cancel. As time passed I decided to stop blaming myself and accept the ways I was complicit in my own pain. I know that God has something even better for me.”

6. …And realizing you really are over him

Kim Coles, Actress and Comedian: “I dated a guy I knew was no good for me from the start. He was a brooding puppy I thought I could help. After a few months of his controlling ways and verbal abuse, I had had enough and said it was over. He demanded we remain friends. In one conversation he went on and on about himself and I finally snapped. I cussed him out and told him to lose my number and to never call me again. I then got a tattoo that said ‘Goddess’ on my left wrist to forever remind me to allow myself to be valued like the queen I am. In that moment I knew there was no way I would ever let anyone treat me badly again. Now I have an amazing relationship with a man who treats me the way I deserve and demand.”

7. Finding a love that makes all the crazy worth it

Niecy Nash, Actress and Author: “I was active on the single scene when I met my husband Jay. As a divorcée, I knew I wanted to love again. During our third month of dating, I was on the phone complaining about an upcoming meeting. I wasn’t sure if he was listening, and we hung up. The next day I had an e-mail that said, ‘Hey, babe, I made notes on your concerns. Attached is a Power- Point presentation in case you need it. Have a great meeting.’ In that moment I decided to let myself love him.”

8. Enduring a major #fail with your relationship intact

Cynthia Bailey, Model and Style Entrepreneur: “My fibroids got worse as I got older. With a heavy cycle, I wasn’t much interested in sex. One night my husband, Peter, and I had dinner with another Real Housewives of Atlanta couple. Afterward, I stood and felt a whoosh. He saw my panic and walked behind me. In the elevator I could feel liquid down my legs and soon was in a pool of blood. Peter took me to the room and had someone clean the elevator. Soon after, I had a uterine fibroid embolization. I got my life and sex drive back.” 

9. Cohabitating with your boo

Charli Penn, ESSENCE.com Relationships Editor: “My husband and I moved in after a year together. I had to learn to share a bed with a grown man and a lazy dog and cook meals when I was a frozen-dinner girl. Thankfully, the perks outweighed the problems when I heard a bump at night and had him there. Now I get to go home to my best friend.”

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