Date #1 - Derrick, The High School Guidance Counselor

How We Met

Derrick and I have spoken before we there was even a thought about seeing one another on a “get to know you better” level. You see, Derrick used to be my daughter’s guidance counselor at her old high school, so it’s not like he’s a total stranger to me… even though we only met once before.

One night, about a month ago, I was perusing a dating site and I received a message from him. In his message he stated how beautiful he thought I was and that I looked very familiar. Of course I went over to his page to check out the other photos of him to see if I recognized him but I didn't. We went back and forth exchanging messages for two days before he asked if he could call me. Although the messages we sent were pretty cool, he came across very business-like and impersonal, almost uptight, but, we all know words via email/text can be conveyed one way when they are meant a totally different way. I was a bit apprehensive at first, but I had to admit that I was intrigued as to why such a good looking guy with no kids, educated, and who seemingly had his shit together was still single? So I gave him my number and he called immediately. As we talked, he began telling me about his job. So I asked, “What school is this that you’re at?” and when he told me, I instantly remember who he is. I tell him that my daughter used to attend that school. He asks her name and I tell him. Low and behold, he was her guidance counselor her freshman year. Now, no one would think that just by having this small commonality that they would be subjected to a full on background check… but I was. What Derrick had, that no one else that I had ever just met, was my real name. I don’t give that to ANYONE! It’s not like I’m running around here being someone else with a fake name because I’m not. I don’t really care for my birth name, so I don’t use it. I use a name that I have used my entire life. Only close friends and family know my real name. After a few minutes he begins to spout off several places where I have lived over the last few years, a minor infraction that I incurred back in college and a few other things. Talk about heated!!! I was beyond it! Yes, I know that with the internet you can find anything you want about anyone now days, but good grief Charlie Brown! Really? He told me that it was no big deal, but to me it was. The conversation continued for another 20 minutes or so, but by this time, it had lost all the newness and sparkle experienced when you first meet someone. I was ready to call it quits on this one already. He text me the next day, but I had already lost what little interest that I had.

Three weeks would pass before we spoke again…

The Date

When Derrick reached back out to me after that first mishap, again, I was apprehensive, but this time I expressed to him why. When I let him know, he explained to me again that he didn’t mean any harm and that he was sorry. I accepted his apology and he asked if he could make it up to me by cooking dinner for me. I was game for the idea at first but later thought about it. I don’t want our first date to be in such a personal setting. Anyone who knows me, knows that I’m a pessimist (but I’m working on this) and I was thinking of all of the negative things that could/would happen if at his place; what if he said something and I got mad? Here I am at his place and it would be awkward. What if he’s some undercover sexual deviant and tries to rape me. I know that one is crazy but shit like this happens. So many things ran through my mind on this.

I called Derrick and told him that it would be best if we met somewhere neutral for our first date. He attempted to reassure me that nothing would happen that I didn’t want to happen (I’ve heard that shit before) and that he would be on his best behavior.

"Uhhhh, is your best behavior only reserved for when you’re entertaining someone at your home?”, I ask.

"No, no, no, I know how to conduct myself at all times.” He responds.

“Wonderful!”, I add, “So where are we meeting at?”

I couldn’t give in on this one, no matter how much he reassured me and no matter how great of a cook he claimed to be. If all goes well, maybe I’ll get another opportunity to taste his wonderful cooking.

We decided on bowling for the first date. He asked if I bowled and I told him that I have before, but my skills weren’t up to par like I was in some kind of weekly league. He chuckled under his breath and asked,
“Wanna put a friendly wager on this game?”

Leary, I ask, “What kind of wager?”

"Winner gets a massage!”

SAY WHAT NOW?!?!?!?!? C’mon dude, we all know the old massage trick and we know where it goes once it gets started, so hell to the naw!!!… out of the question! I let him know that I wasn’t with that plan, so he concedes and says the winner has to buy the loser dinner if there is another date. That’ll work!

We planned to meet at the bowling alley by 9:30 p.m., only because I had to pick my daughter up from work at 8:30. By the time I made it home to get ready it was 9:00 p.m. It was a 30 minute drive to the bowling alley, so clearly I wasn't going to make the time. I called to let him know I’d be late and he informed me that he was still at the school but to call him when I was leaving my house since he was closer and it would give him time to get home and get ready. I didn’t leave my house until 9:45. When I pull into the parking lot of the bowling alley, there is a group of people out front. At first they were all just standing around talking, but I should have known better. As I sit in my car waiting, I call Derrick to ask his whereabouts and he tells me that he’s five minutes away. Once we hang up, I hear a bunch of commotion outside. I get out of the car only to see two idiots and their band of dullards dancing around around one another getting ready to fight. Great! He’s brought me to the hood bowling alley. At this point, I’m ready to leave his ass high and dry and take my behind home.

My phone rings and it’s him. He’s arrived but can’t get into the parking lot because these idiots are blocking the entrance. Finally the crowd disperses and he pulls up next to me. I didn’t want to get out of my car. I didn’t know what was going on or if someone had a gun or what! He gets out and pulls on my door handle for me to get out. I edge down my window and ask if the coast is clear. He tells me everything is good and we both laugh as he asks me to get out. After all of this, he still wants to go inside to bowl. I already knew what was going to happen. If the crowd outside was any indication of what the crowd was like inside, then we weren’t doing jack shit in that bowling alley on this night. As expected, it was teeny bopper, let’s turn the bowling alley into the club night and we do an immediate about face back out the door.

Now what? He is clearly adamant about playing me in a game of something or other because he suggests that we go across the street to TacoMac to shoot a few games of pool. Again, he asks if I play pool and I tell him I have, but I ain’t no shark. Before we get back into our cars, he asks for a hug. I know these tricks man. He's trying to get a chest feel of my boobs and slightly graze my behind *eye roll*. As he hugs me, he squeezes me tight and whispers in my ear, “Guidance Counselor Derrick left at 3 o’clock, don’t expect this to be all business like on the phone.” Talk about chills up and down my spine... *good laaawdy miss clawdy*!!! He flashes a big grin and opens my door for me to get in my car. 

As we pull into the TacoMac parking lot, it’s packed and as expected so is the inside. We leave without going in and we’re back on the hunt for somewhere to go. As we’re driving, I notice that my car was getting low on gas and I needed to fill up. I call him and we stop at a gas station. I get out and so does he. It’s about 30 degrees outside and the wind is cutting right through me. I take out my card to put in the pump and he lightly slaps my hand and tells me to put my card away. Pssshhh... you ain’t got to tell me twice! I put my card back in my wallet and he says, “Okay, now go and sit in the car and I’ll fill your tank.” *blank stare* Really? Fill it? Not just put in $10, Which would only make my car burp? Sure enough, he puts in $56 and I couldn’t be happier. I open the door to thank him and ask where we’re going and he doesn’t say anything, just smiles.

We end up at a sports bar called Skyboxx. I park in front of the bar and he parks on the other side. As I’m getting out of my car, a guy starts my way and says,

“Hey, your girls are inside waiting on you.”

I turn around to see if he was talking to someone else. He points at me and says,

“You! I’m talking to you!”.

“You can’t be talking to me,” I say, “because I’m not meeting any women here.”

He edges closer,

“Oh, so you’re here to meet me then I guess?”

LAME! As he continues to walk up, I see Derrick approaching out the corner of my eye,

“Actually brotha, she’s here to meet me.”

*AND THE CROWD GOES WILD*

Why I got all warm and goopy on the inside I don’t know… maybe it was that moment that we all see in the movies where you think all hope is lost for the poor female character and then, out of know where, here comes Mr. Wonderful to save the day. Yup… that would have to be why. The guy backs up and says,

“My bad homeboy, I didn’t mean no disrespect.”

They give each other a quick pound and I never noticed the beautiful bouquet of flowers in Derrick's hand. He turns to hand them to me and I get the cheesiest grin like the Cheshire Cat from Alice in Wonderland.

I’m embarrassed to admit that I’ve never had a man actually bring me flowers on a date, so this was a welcomed surprise. I give him a kiss on the cheek and thank him before I put the flowers in my car.

We spent the next two hours laughing and talking about any and everything. I didn’t want it to end and neither did he. It’s 12:30 and the bar is closing in 30 minutes. He asks if I would like to come back to his house and we could watch a movie On Demand. Even though I was apprehensive at first, all of those feelings were squelched by the time we were ready to leave. He promised that he wouldn’t try anything and that we would only watch a movie and talk if nothing else. Hmmm… I know what you’re thinking, “DON’T DO IT GIRL” “HE’S GOING TO TRY TO GET SOME BOOTY!”. The part of me that was tired told me to take my butt home and call it a night, but the larger part of me that wanted to continue to spend time with him was screaming, “You better get yo black ass in that car and follow him to his house!!!” One should not deny themselves of indulging in the unknown every now and then, so, off we went.

We made it back to his house and I was beyond impressed. Not your typical bachelor pad at all. This place looked like the model homes that are staged for potential buyers to fall in love with upon first sight. An old organ, an antique wooden bench and one of the biggest full sized mirrors I have ever seen in my life sat in the foyer as you walked in. Beautiful crème/chocolate traditional curtains lined the windows. All of the furniture was chocolate brown and the rugs were multicolored. A fairly large flat screen t.v. hung above the fireplace with the surround sound speakers in every corner of the living room. I sat on the couch and he turned the t.v. on the jazz station and lit the fireplace before excusing himself upstairs. Talk about setting the mood. Geesh!!! I had to continue to talk to myself to keep from getting woosy from the ambiance. As I looked around, I noticed three bowling trophies sitting on a shelf in the corner. That punk! No wonder he was trying to play for a massage… because he knew he’d more than likely win. He came back downstairs wearing sweats and a t-shirt from his alma mater, Morehouse College. Might I add that the tee fit quite nicely around the arm and chest areas *ahem*. I silently shook my head and had to calm that little voice that kept saying that I was putting myself in a dangerous (not in a bad way) situation.

He comes around the corner with a box in his hand, and I instantly got excited. It’s my favorite game, Scrabble.

“I remember that you said that you liked this game, so I figured what better way to get that match we’ve been trying for all night,” he says.

This was very thoughtful. That he would remember something like this from me mentioning it one time in a conversation told me that he was actually listening when I talked. Naturally, I win both games, which take forever. It’s now almost 3 am and I am dog tired and he can tell. He asks if I want to stay and just leave early in the morning. He tells me that I don’t have to sleep in his bed; that he has 3 spare rooms and I can choose one to stay in for the night. As tired as I was, I knew that would have been a bad idea. I was really scared to drive home though. I was more than tired; I could barely keep my eyes open. But I couldn’t allow myself to get home around the time my daughter was walking out the door to go to school, so I told him that it would be best that I leave. Before leaving we hugged again, and this time, he kisses my neck. THAT is a no no... a definite NO NO!!! As he kisses my neck, he works his way up slowly to my lips and yes, I kissed him… And I do mean KISSED him! In all honesty, had I not lived so far away, after that kiss, I probably would have stayed. Just being honest! Nevertheless, he talked to me on the phone the whole way home and I was greatly appreciative. Especially since he had to get up and get ready for work in two hours. 

I must say, even though this is date #1, it is going to take someone/something damn near extraordinary to top this one. It wasn't about being attracted to him, because initially, I wasn't. He's shorter than me, not by much, but still and he has a bald head, which I usually don't like. But those are inconsequential things that don't hold a candle to how I felt throughout the entire date. It was fun and totally comfortable.