October 2008

[Song playing from cars on the streets of Chicago]

Dear Diary,

I can hardly believe it. I left DC to volunteer at Obama HQ in Chicago for 10 weeks to elect the first Black president of the United States! Eek! I’m so blessed to be here and, let me just say: Chicago has really blessed me with all these fine ass men walking around!

I’ve got a funny little tale to tell about one such fine ass Chitown boo named Shawn. Tall, mocha brown, funny man I met through my friend who lives on the Southside. She invited me to her work happy hour, and when I ended up talking to her boss, he made me laugh so hard that at the same time I took a sip of my drink, I snorted it through my nose. Not a sexy move, but an authentic one. He asked me out on a date, and I obliged. He introduced me to old-fashioneds, explained why sophisticated people order steak medium-rare, and told me he was going through a divorce, even though he was still wearing his wedding ring. Suspect, for sure. But whatever, I’m in Chicago for a good time, not a long time.

Fast forward a few weeks, and the man has been coming on strong. Calls every day, texts every night, and makes me feel like I’m starring in my own grown and sexy rom-com. When we’re out together, he opens doors, orders for me, says all the right things at all the right moments. For once, I thought this one might actually be different. Chicago men might be built better than those dusty D.C. dudes.

Then came the night that changed all that.

Shawn said he wanted to take me somewhere special. “Somewhere just for us,” he said. His tone was smooth, low, promising.

The anticipation inspired an outfit costing more than my rent: a silky low-cut Black dress, suede high heels with an ankle bow by a designer whose name I can’t pronounce, perfume that naughtily whispers “fuck me”, and a lace underwear set for the gods.

He picked me up in his luxury vehicle, looking as fine as ever. Confident, cologne drawing me closer in, smile doing overtime. We drove away from downtown, the lights thinning out, the streets getting quieter. I asked where we were going. He just grinned and said, “You’ll see.”

And oh, I saw.

We pulled into a motel. Not a boutique hotel. Not a charming little inn. A motel. One of those places with a flickering neon sign where the “Vacancy” light hums louder than your intuition.

My heart dropped to my knees. I thought he was stopping for directions or to make a call, but then he parked. And turned off the car.

I wanted to say something. I should’ve said something. But then he reached over, took my hand, and smiled that same smooth smile from when I first met him, the one that had me thinking maybe I’d finally found a grown man who got it.

Inside, the room was a time capsule from the 1980s. Red velvet curtains. Cigarette burns on the carpet. A mirror on the ceiling that has probably seen too much. And then, the pièce de résistance, a heart-shaped bed with satin sheets and a coin slot on the nightstand.

He opened a twist-top bottle of cheap champagne and put some money in the slot to make the bed start humming like a clothes dryer.

I sat on the edge, trying to keep a straight face while thinking about what had led me to this vibrating monument of bad judgment.

Shawn, unbothered, started unbuttoning his shirt, grinning like a man in a music video no one asked for. I’ll admit, it was working. For a hot minute. Until he unzipped his pants.

Red.

Thong.

Underwear.

I blinked. Blinked again. Because surely, this was a joke. Surely, he was doing performance art. But no. He was standing there, like this was the big romantic gesture he’d been hyping up all week.

“Do you like it?” he asked, flexing his dick in the thong just a little bit.

All I could do was take another long sip of that bad champagne.

I was too stunned, too deep into curiosity, and too entertained to exit stage left.

We ended up making all sorts of kinky decisions on that ridiculous red bed.

A beautiful Chitown Black man with charm, intellect, and Obama-era swag with a proclivity for thongs and pay-by-the-hour motels. Isn’t life grand?

[Song that played at the speakeasy]

Dear Diary,

He looked up from staring straight at my breasts and said, “Oh, I’m sorry. What did you say?”

That’s when it hit me. I was sitting there in my brand-new $168 dress, $100 hair-do, $50 in fresh MAC makeup, $40 mani-pedi, $15 cab ride, and hours of prep for this date that turned out to be an expensive lesson.

Back in 2006, when I first met him, he gave off that whole “renaissance man” vibe. Confident but not too cocky, well-traveled, sharp, funny. The type of man who could make you feel like you’d leveled up just by being near him. I was intrigued.

Fast forward to this year. I get this random GChat message out of nowhere. “You? Online dating? No way you need that.” I laughed. He was referencing my GChat status that read: “Dating apps are the absolute worst.” Same old smooth talker. We started chatting again, casual, harmless, slightly flirty. I mentioned I was working on my grad school statement, and he offered to help. Given his whole Yale-Rhodes Scholarship-world-traveler-author résumé, I figured, why not? He actually made the statement better, so when he said he’d be in town for business, it felt like a nice full-circle moment. I said yes to drinks.

We met at this new speakeasy uptown that needed a password to get in. Cozy place, dim lights, real moody. I looked amazing. He looked… okay. Maybe a 7 on a generous day. Gaps across multiple teeth, hairline fighting for its life, and this smug grin that told me his ego had been eating protein and working out since the last time I saw him.

Ten minutes in, I wanted to leave. Every conversation turned sexual. I asked him about his career. He told me about his “wild time” in Brazil. I wanted to talk about going to grad school. He brought up our “chemistry.” I said I was struggling to make new friends. He asked if I’d at least been getting laid. He bragged about flying his exes out for “casual fun.” I just kept sipping my drink and counting down to the moment I could leave without it being awkward.

Then he switched gears. “So,” he said, “You went to Chicago to work for the Obama campaign. Did you ever get to meet him?” I said no, already bracing myself for the flex I knew was coming. Sure enough, he smirked. “I mean, my father hosted a fundraiser for him. So, yeah, I’ve met him a few times.”

I nearly rolled my eyes right out of my head. He was dripping in arrogance, thinking that would make my pussy drip. I realized right then that this man didn’t want a date. He wanted to collect another pussy stamp on his little global conquest card.

But he didn’t know who he was dealing with.

Years in this city will teach you plenty about men who look good on paper, but ain’t shit in real life. I’ve dated them all: the broke dreamers, the fake hipsters, the self-proclaimed rebels, the wannabe intellectuals. I thought this one would finally be someone on my level. Turns out, the only thing he had more of than passport stamps was ego.

Somewhere between his bragging about sleeping with women all over Latin America during his gap year and explaining “levels of prestige” in the legal world, I realized something. He wasn’t testing me. I was testing myself, seeing if I’d still fall for the same type of man who mistakes arrogance for depth.

The old me probably would’ve. But not tonight.

I leaned back, looked at him in those self-satisfied blue eyes, and said, “Thanks for the drink. I’m gonna head home.”

It wasn’t just self-control. It was growth. I know what I’m worth. No degree, no passport, no Yale pedigree can compete with that.

[Song on her childhood boombox radio as she journals]

December 2005

Dear Diary,

Good ol’ home for the holidays. This is the first Christmas holiday as a fully fledged adult working woman, and it’s been fun commiserating with all my high school friends who are back home too, especially [redacted]. I mean, I’ve loved him since I laid my eyes on him when I joined the school newspaper as a writer in 9th grade, and he was a contributor too. I just couldn’t wait to have some one-on-one time.

After we graduated from college, we began to get a little closer (a.k.a. making out). To be honest, I was so excited at the possibility of falling in love with one of my best friends. Well, I remember calling him one day, soon after we had begun sharing more intimate moments, and I wanted to really see him again. He expressed to me he was “broke” and couldn’t take me anywhere nice. So, in an attempt to be accommodating and to find a way to see him again, I decided that a cute lunch date at his house would suffice. I could cook something cheap, like pasta, with a side salad, and we could just relax and talk at his house. Besides, I was a friend from way back that he didn’t need to impress. He liked that idea and actually offered to buy the necessary groceries for the meal, which would include the following:

1. spaghetti pasta

2. ground turkey (tryna be healthy, ha!)

3. onion

4. lettuce

5. tomato

Yep. That’s it. He already had olive oil, spaghetti sauce, salad dressing, and any spice that I would need to make the meal. So, I just knew that we would meet in two days. I couldn’t wait!

The following day, I called him to confirm what time we would be meeting, and the following conversation transpired:

“Hello,” he answered.

“Hey there! How are you?”

“I’m pretty good. How are you?”

“I’m doing alright. I just wanted to call and find out what time you wanted to meet tomorrow,” I said, trying to suppress the excitement in my voice to keep it cool as if I didn’t really give a fuck.

“Didn’t you get my text message earlier?”

“No. Why?”

“Oh. Well, we are going to have to make it for Thursday instead of tomorrow.”

“Oh, really? Um, I think I can do that, but why can’t we meet tomorrow?”

“Aw, man. Well, my Mom came home today and dropped a bomb on me, man.”

“What happened?” I asked with concern.

“Well, she said that she’s not going to the grocery store today. She’s going tomorrow instead. So, we are going to have to wait ‘til Thursday.”

I paused and tried to understand what he was saying. “Um. Wait. I don’t get it. Why can’t you go to the grocery store by yourself?”

“Because if I go with my Mom, the food will be FREE!” he said with genuine elation.

Yes. That was the conversation. I couldn’t believe that he had the gall and audacity to tell me that. No embarrassment, no shame, no hemming and hawing, as Mom would say. In my mind, I thought, are you telling me that you couldn’t even buy a few items at the grocery store that would have been the equivalent of maybe $8? Damn! You a broke ass bitch!

I still went over to his momma’s house on Thursday. Ha! But his broke ass made my pussy dry up, so that holiday make-out session stayed a fantasy.

[Song playing at stroke of midnight]

January 2007

Dear Diary,

New Year’s Eve was a night of many firsts. First time going to a club on New Year’s Eve. First time going to a club alone. First time to have sex on New Year’s Eve.

Let me introduce you to Big Willy Style.

I met Big Willy Style much earlier last year at a bar in Bethesda, Maryland. He was my bartender, and I thoroughly enjoyed flirting with him. He was decent-looking, but that was not what made him attractive. He made me realize that in D.C., it doesn’t take much to impress a woman because the overwhelming majority of men put little effort into anything they do for women. The bare minimum is the order of the day. Well, he stepped it up a notch. We began to date, and he took me to nice restaurants and always let me (and my girls!) into the club FOR FREE! We were delighted with this arrangement. Again, a little goes a long way in this town.

We never went past kissing all year, and he never pressured me to do so. I appreciated that, of course. When New Year’s Eve rolled around, I knew I wanted to go somewhere fun with friends, but found myself alone once again since all my close friends went home for the holidays. Boo-hoo. So, I called Big Willy Style and decided to go to his club all by my lonesome. And I ended up having a lot more fun than I bargained for.

The night was great! People were out to have a good time. I talked to a lot of people, and Big Willy Style took care of me. Drinks were taken off the check, and food was taken care of. I couldn’t have asked for more except for my friends to be with me. At the stroke of midnight, we kissed the New Year in, and I remembered why he made me feel so great. Then he looked at me and said, “Come to my office.”

I followed him upstairs to his office, and as he closed the door behind him, he began almost violently to kiss me like my mouth was his favorite home-cooked meal. It was good. Really good. He held me so tightly like he wanted to swallow me whole. Then, he said, “I want to show you something.” He unzipped his pants and showed me his gigantic, thick, long, throbbing, out-of-this-world dick. I mean, my jaw dropped to the floor and I did not blink for at least 20 seconds. I couldn’t believe it. It was so…pretty. I never knew a dick could be such a thing. I was in love. If I were an animation, I’d have hearts for eyes and stars above my head. He saw the look of amazement on my face and smiled. I could’ve devoured him then, but he had to go back to work. Then I said, “When you get off tonight, call me.” And the rest is history. I literally brought in the New Year with a “bang.”

June 2006

[Music coming from the speakers as she journals about how Google saved her life]

Dear Diary,

I met this nice white boy on the Metro who seemed interesting enough. We both rolled our eyes at the same time, frustrated by the wait for the next train…more than twenty minutes! A match formed over public transit woes in DC. After chatting a bit, we learned we lived in the same neighborhood. He asked if I’d be down to catch a cab together instead. Hell yeah! A man who takes initiative and can have an engaging conversation. Let’s go! After the cabbie drove us through three different cab zones, he paid the fare and asked for my number. I obliged. He was cute, could put sentences together, and lived in my hood. Why not?! He called me the next day to ask me out on a date, and I replied, “Sure.” I may have been a little too anxious about it, as I was excited about the chance to go out on a “real” date.

He took me out to Maggiano’s, an Italian restaurant not too far from the Friendship Heights Metro. Our conversation again was very engaging. He had good table manners and was dressed nicely, so the date was going well. But then, the check came. Now, this is an interesting part of any date as the woman either expects that the man who asked her out will pay for it or she hesitates in saying “We can split it, if you like.” Well, my date reached into his pocket and pulled out, not a wallet, but a WAD OF CASH! It had to be at least $1,000—a STACK, jack! It was an insane amount of money that was wrapped with a rubber band. I had an expression on my face that said, “What the hell?!”

He then said, “I mean, you know. I’m a gold digger. I like money. If you were to come to my house, you would see stacks of bills in my room. Whenever you go out with me, you know I got you. Money is never an issue for me. I always make sure I have enough cash flow, aight?” His ghetto fabulous talk had definitely shown brightly at this point. So, I just shrugged my shoulders and was happy I didn’t have to pay.

A few days later, on a Sunday, he called me and left a message on my cell phone saying, “You will never believe what I’ve been doing all weekend. I googled you and found out all types of interesting information. I saw you all over your college’s website. It must be nice being you.”

Okay. I was freaked out. Googling people isn’t that strange, but you don’t TELL someone about it! Well, nonetheless, I decided to meet up with him to get dinner. While at dinner he said, “Yeah, if you google me, you won’t find anything.”

So, his sorry attempt to deter me from googling him was not going to work because of course I would google him. I typed in his first name and then his last and, alas, I didn’t find anything. Then, I had a small voice, or maybe an ancestor, in my head tell me, “Type in his name and then the words ‘Washington, DC’ afterwards.” I did that and I found the most astounding, jaw dropping, unbelievable information.

It was a website that was from a county in Virginia and they had a service called Crime Solvers. It had a mug shot of the guy I had been dating and said the following:

“Warrant for his arrest for failure to appear in court for a suspended license, domestic assault, and carnal knowledge. If you have any information about this individual, you can receive up to $1,000.”

I freaked out once again. I knew it was him because his freaking mug shot was next to the information about him. So, I called my Aunt, a prominent lawyer in Cleveland, to ask what “carnal knowledge” meant. I mean, I could have googled that too, but I needed to bring in my favorite auntie on this news. In a nutshell, it is sex with a minor!

So, this explains the wad of cash thing, because he probably had to get paid under the table for whatever “job” he did, since he couldn’t apply for a real job with a warrant out. Wow.

Now, of course, communication with him had to cease; this was not in question, but I did contemplate turning him in, reaping the benefits, and getting my own stack!

October 2007

[Sounds coming from the bar’s sound system as she journals]

Dear Diary,

So…I went out with this guy who apparently has a semi-criminal past, so I’ll call him Desperado. I first met him at a restaurant in D.C. He was my server. I swear, I have a thing for servers. It’s a recurring theme. Maybe the power dynamic? Anyway, I thought he was decent-looking when I first saw him, but I honestly didn’t think much of it at the time.

Then I bumped into him again on the Metro, Columbia Heights stop. I struck up a conversation, and he asked for my number. I gave it to him, thinking it really wouldn’t go anywhere. But the next week he called and asked me out. I said yes.

We went to a local bar, and the conversation was easy enough. Except… he kept talking about his wild exploits in Latin America, claiming he fought alongside Colombian guerrillas and even saved his father from being killed. I wasn’t sure how much of it was true, but I went along with it. Who am I to argue with someone’s story, especially if they’re the one buying the drinks?

Obviously, because he apparently narrowly escaped death, I had to go home with Desperado. I still don’t know what I was thinking. Honestly, I was bored, and the idea of going home alone just didn’t sound that appealing.

We immediately started kissing, touching, and fooling around when we entered his place. Then he slowly, almost ceremoniously, took off my underwear with so much reverence as if it were a ritual among the gods. I closed my eyes, anticipating his touch, expecting his hand or mouth… but instead I felt him move away and sit at the end of the bed.

When I opened my eyes, I guffawed. He was smelling my underwear. Smelling. My. Underwear.

He looked at me and said, “You just don’t know how much this turns me on.”

And I said, “You just don’t know how much I’m grossed out.”

Needless to say, I never spoke to him again.

[Sounds of mid-aughts playing from her stereo as she opens her diary]

April 2006

Dear Diary,

Got a little tale about a man I’m dating. I’ll just call him, SAD.

It is springtime now, and for me, there is nothing like this season to inspire me to find love in everything. The bright blue skies, the promise of summer, the temperate winds, the marshmallow clouds, the cherry blossoms in April. D.C. is so easy to fall in love with during this time of year, and just as easy to want someone to share it with, even if only briefly. So, I’m happy SAD came into the picture.

Good-looking, intelligent, well-dressed SAD. As I’ve gotten to know him, I’ve been impressed with his maturity and his patience with my carefree attitude about life. I decided to give him a try and go out on a few dates. We’ve visited museums, watched movies, gone to nightclubs, and introduced one another to friends. Everything has been moving at a good pace.

We shared our first kiss two months into dating. I know, two months! Really, really sweet. As I said, he is a very patient man and will not pressure any woman into doing anything she does not want to do. Perfect, right? Last night, after I arrived home from playing a co-ed softball game after work, he called me:

“Hey, what are you doing?” he asked.

“Just got home from playing a softball game. How are you?”

“I’m pretty good.”

“That’s good.”

He asked, “Did you all win?”

“You know it. We are getting better now.”

“Good. Good. Hey, I have a question.”

“What’s up?”

He asked, “What if I said I want to come over tonight?”

mmmmmm. I bit my lower lip at the proposition.

I said, “Um, sure, I guess. It’s Tuesday, and it’s almost 10 pm, but if you'd like to come over for a little while, that’s fine. You live in Rockville, though, right?”

“Yeah, but I haven’t seen you in a little while, and I just want to come over and see you.”

“OK. How soon can you get here?”

“About 30 minutes.”

My heart fluttered, and I was so excited. In those 30 minutes, I showered, curled my hair, and cleaned up my place. That’s right. An anxious and horny girl can pack a lot into a short amount of time. I was not sure what to expect, but I wanted to be prepared for anything.

And then there he was. SAD walked through my apartment door, not looking quite as sharp as his normal get-up when we went out. This time, he had on sweats and a baseball cap on backwards. Whatever. It was sweet that he decided to drive 30 minutes just to see me. We hung out, chatted, and laughed. Then he kissed me. Very nice. He took his shirt off and revealed one of the most beautiful bodies I have ever seen. All that working out he told me about was paying off. I was impressed.

We kissed and kissed and kept on kissing. I decided to turn up the heat a little bit. 2006 is all about turning up the heat, ok?! I began kissing his chest and torso, and then began to pull down his sweats. As my lips trailed down his six-pack, I decided to be a naughty girl and pull down his boxers as well…

But I could not go that far.

Why not? Because when I began to pull his boxers down, something hit my face like a steel pan. At first, I was too delirious and shocked to comprehend what was happening. Then I realized.

It was the most pervasive and revolting smell to ever emanate from a man’s balls that I had ever smelled in my life.

That’s right. Smelly. Ass. Dick. The air around me became thick and musty to the point where I was afraid to breathe. I was in fear of becoming noticeably sick. The lights in my apartment were still on, so I knew he would see my disgust and repulsion.

I pulled his boxers and sweatpants back up and told him I was actually getting tired and should go to bed. He believed that excuse. To this day, he has no idea why I never called him again.

Remember: if you visit someone’s house that you are dating, especially at night, whether you think you are going to hook up or not, you should take a shower and be presentable out of respect. Damn!