"I don't know, I just don't see the problem with using a LivingSocial coupon on a date."

Let a man tell it and he’s never lost in love. He’s always been in control and never once experienced heartache. I have friends who say they’ve never been dumped. The problem with that line of thinking is it doesn’t account for all the women who just outright rejected them. I’ll admit, it hasn’t always been safe landings, sunny days and moments of legendary greatness for me. There have been times when I’ve been angry, upset, hurt or disheveled so much that I had to sit back and laugh. In this two-part series, I’m going to tell six stories about mistakes I’ve made in my past. These are the first three. I hope you’ll enjoy.

February 14th, 1992

There’s a few things that I remember about 4th grade: I finally found a sport I was good at; I would always have to avoid Cassandra for the rest of my life; and I finally got to sit at a table with a pretty girl. At the beginning of 4th grade, I noticed that no matter how much I grew over the summer, Cassandra always grew an inch or two more. All that didn’t matter much– what mattered the most was that I was sitting at the classroom table with Latondra, the fourth prettiest girl in school. Latondra was pretty and I liked her. She had pretty brown eyes, hoop earrings with her name in gold and not too many scars. She had a small scar above her lip because she mistook the slides for a water fountain one day during a game of tag. However, it wasn’t her looks that attracted me to her. I liked Latondra because she talked to me. In 4th grade talking to a boy was enough for him to develop an obsession.

There were four people sitting at our table: Kiana, Latondra, Robert and myself. The only reason I remember Kiana and Robert is because Kiana showed me at an early age that society typically chooses complexion over beauty. I remember Robert because he was the only person in school shorter than me. I was trying to be suave and planned on doing something special for Latondra on Valentine’s Day. I wasn’t just going to get the candy with the names on it; I was going to surprise her with something romantic. I got her flowers, drew her a picture, gave her a pack of gushers and a card that I handwrote. On Valentine’s I walked into class with my gifts all in a Safeway grocery bag and placed them on her desk. The whole class looked at me and I look at Latondra and said, “Would you be my Valentine?” She had this stunned look on her face. Our teacher, Ms. Taylor looked at us and said, “Aww… that’s so sweet.” My entire class busted out laughing. The worst part, so did Latondra.

See Also:  The Ugly Truth

Lesson Learned: Stop simping.

The Flower Fiasco

I had this strategy of getting first dates with women. I would give my phone to women when I met them. Just straight up give the phone to them and walk away. Why? If she had my phone, then we’d have to meet up later for me to get it back. Her friends read this blog, so I’m going to call her, Courtney. I met Courtney at a club in NYC. I was enamored. We had been talking for most of the night and my boy wanted to leave. So I asked her, “Would you mind if I got your number?” She replied, “Sure, why not?” I handed her my phone and said, “Do you know how to use one of these?” As soon as she started to type in her number, I left the club. Two hours later a mutual friend calls my boy while we’re at an afterhours spot and told him that Courtney had my phone. We arranged to meet for brunch to exchange the phone. Yahtzee! 

After brunch and retrieving my phone, I decided to do something nice for her. I decided I’d get her flowers–roses, three dozen in total. I had them delivered to her at work. One problem: she works in a hospital. Regardless, I had faith in the power of modern medicine that if the flowers were delivered to the hospital, they’d be able to find one of their own employees. I got a confirmation that the flowers were delivered, but heard nothing from her. I asked a mutual friend, “Hey, did she get any flowers?” Her friend told me she hadn’t received anything. After talking to the florist and the hospital, we agreed that it would be more helpful to deliver them to her area of the hospital. Second problem: she works nights and the florist doesn’t. Again, I had faith that they’d be able to figure it out; they didn’t. Finally, I had to tell her that I sent the flowers, so we could try and find six dozen roses that were floating around her hospital. She told me that she really shouldn’t be the one to find them. I still don’t agree with that part, but then she said, “Why not just send them to my house?” Albeit five days after the original delivery, I did that and she got them. Her text to me, “I got the flowers, thanks!” I thought she could have reacted differently after all the trouble I went through getting her the flowers. She thought that the process of her receiving flowers was too arduous and overshadowed the nice gesture.

See Also:  When Bad Conversations Happen To Good People

Lesson Learned: Don’t buy anyone flowers other than your mother.

The Kennedy Center

I love the Arts. It’s been a love of mine since I was young. When I really like a woman, I try and gauge her love for the Arts, too. Here in DC you have a lot of options, you can typically catch free shows at our museums and parks. If you really want to impress a girl, you’ll take her to the Kennedy Center. The Kennedy Center means you have to dress up, have a nice dinner, and get your “grown man” on for a few hours. I was seeing this young lady and in an attempt to impress her after we had been on a few dates, I decided to take her to the Kennedy Center. If you take a girl to the Kennedy Center, she had better be special. It’s going to run you at least $200 for the date without alcohol. After the Kennedy Center, I was kind of feeling myself, the situation and where things were going. I was respectful, never pressing the issue of sex or commitment. I just took my time and thought that by being a gentleman it would pay off in the end.

A few more weeks went by and it was her birthday. I had to make the decision to attend or decline. If you’re not in a relationship with a woman, attending her birthday party is a big risk. You can either end up being the focal point of her night, or insignificant. I chose to go; we hung out and had a good time. Drinks were poured and the night was about to come to a close when I had the option of taking things a little further that night. I declined for a few reasons: 1) She had been drinking and I didn’t want the first time to be under the influence; 2) I was still trying to show her that I was a gentleman; and 3) I wanted to hold out as long as possible to increase her interest. I know #3 seems like a bad idea, but … actually nevermind, I’ve already said too much.

See Also:  The Good Man vs Bad Husband Syndrome

It seemed like a good idea, but it was her birthday; she was going to have a good night if she wanted. It felt as though I walked away for a moment to talk to some friends, when another guy swooped in. She ended up spending the remainder of the night talking to him and a few weeks later she would be dating him. My boys asked me what happened and all I could come up with was, “I took that girl to the Kennedy Center, man.” 

Lesson Learned: No really, stop simping. 

It’s true, the best laid plans of mice and men often go awry. That’s how I felt in each of these situations. The main point I want to drive home to all of you today is that failure and rejection are a part of the game. I like to sit back and tell these stories when I’m in the barbershop or just kicking it with the guys. Please don’t take this to mean I spent a lot of time in the past losing. As Jamie Foxx would say, “Don’t test my pickle.” Trust, the game’s been good to me ever since I was a lowercase G, but now I’m a big G. I can share all this with you because I’ve learned my lesson. Next week, I have three more stories for you guys. Until then, enjoy your Friday. Be safe, I’m out.

– Dr. J

It’s 4/20. Trippy Mane. Carver The Great put together a great Smoke Break mix today, check it out. Right click and download it here, or stream below. Get your Rihanna on…

Tracklist: 1. Mary 3x by Wiz Khalifa, 2. Marijuana by Kid Cudi, 3. Smoke & Ride by Le$, 4. Party Life by Jay-Z, 5. Bill Gates by Lil Wayne, 6. I Like by Young Swift & Young Jeezy, 7. Amazin’ by Young Jeezy, 8. The Zone by The Weeknd & Drake, 9. Takin’ It There by Young Jeezy & Trey Songz, 10. Take It To The Head by Chris Brown, Rick Ross, Nicki Minaj, & Lil Wayne