It Took Cupid’s Army

It Took Cupid’s Army Can I woo the girl who knows my embarrassing childhood?

Based on a post by Mac G. Listen to the ► podcast at Connected.

Even though it is right in front of you, you don't always see what's good for you. Sometimes you need a little nudge. This is about a couple of mine.

When I was five, Jenny's family moved in directly across the street from us. Our families became good friends right away. Due to the fact that there was nobody else our age living nearby (Jenny is three months older than I am), we soon became inseparable.

She had no trouble keeping up with me in the rough and tumble things I wanted to do, and I had no problems playing house with her when she wanted. One of our parents always had to shoo us home at night because we would never think about it ourselves. I once tried to get my parents to let Jenny spend the night, but they said it was not right for girls to spend the night with boys.

Although I missed it at the time, the first indication that Jenny and I would end up together came when we were fourteen. I was over at her house watching TV with her and her dad. As we sat there, the doorbell rang. Jenny got up to answer it. She came back a moment later followed by a policeman.

"Mr. Adams," he said, "I'm afraid I have some bad news."

Jenny's dad got up to stand next to her. I stood a few feet behind them.

"I'm really sorry to say that there has been an accident. A drunk ran a red light and hit your wife's car," the policeman stated.

"What! When? Where? How is she?" Mr. Adams asked.

"The paramedics did their best, but I'm afraid she didn't make it. I am truly sorry."

At this point, Jenny turned around and looked at me, tears pouring from her eyes. She ran to me, buried her head in my shoulder and sobbed. I guided her to the couch and sat her down. Holding her gently, I let her cry herself out, trying to soothe her as best as I could.

After about fifteen minutes, Mr. Adams finished up with the policeman and came over to sit next to us. Jenny had calmed down a little and was just crying lightly. He took Jenny in his arms and held her. I got up and called my parents telling them what had happened. They both came right over.

After a lot of consoling and grief, Dad left with Mr. Adams to tend to the body while Mom stayed with Jenny and I. Mom told me later how proud she was of me and for handling the situation and comforting Jenny so well. Years later, Mr. Adams said he'd kill me if I told Jenny, but that it hurt a little when Jenny turned to me, instead of him, for comfort upon hearing the news about her mom.

The First Nudge

I have always thought differently about Jenny than anyone else. Even during those awkward adolescent times all boys go through in which girls are gross and have cooties, I never felt that way about Jenny. It was like my mind thought, 'That's not a girl, that's Jenny'. The trouble was that as I grew into a teenager and began to notice girls, it was the same thing; I didn't realize just how beautiful Jenny was becoming.

Ironically, it was on a date with someone else in the summer between our Junior and Senior years that her beauty was pointed out to me. We had been having a great time: Dinner, movie, and ice cream afterwards. It was close to time to take my date home.

"Anne, can I ask you a question?" I asked.

"Sure, what's up?"

"Well, when I asked you out, you seemed a little surprised. Pleased, but surprised. I got the same response from Sarah Jansen last month, and I was wondering if it was true you were surprised, and if so, why?"

Anne smiled and hesitated a moment before answering.

"Yes, it's true I was a little surprised and I'm sure Sarah was as well. The reason is we keep expecting you two knuckleheads to wake up and see what a good thing you've got."

"Knuckleheads? What two knuckleheads?" I asked.

"Okay, it looks like it's up to me to straighten you out, although I really shouldn't," she sighed. "I'm going to do this in a roundabout way. I'm going to ask you a bunch of questions. Some of them may seem silly, and some might be embarrassing, but I need you to trust me and answer them all honestly."

"Okay, I'll try."

"Good. Now first question: Do you think I'm pretty?"

"Of course I do. Most guys in school do."

"Thank you," she said, blushing a little, "Now, I know all guys have different ideas about the ideal woman, but am I your ideal? Be honest."

"No, you're not." I said a little chagrinned.

"Hey, don't worry about it. I asked for honesty. I'm somebody's ideal and I'll find them one day. Let's concentrate on your ideal woman. I'll say an attribute and you tell me what you like. You okay with this?"

"I guess."

"Ok, height?"

"Your height, perhaps a little taller."

"Hair?"

"Red, long and straight."

"Longer than my shoulder length?" Anne asked.

"Yes."

"Eyes?"

"Green."

"Mouth?"

"Don't know. Never thought about that."

"Not a problem. Now, don't get embarrassed, but look at my tits."

I couldn't help it, I turned crimson, but I looked briefly. She had very nice tits.

"That's what I like about you, Tony; even with permission you don't ogle at a girl's chest. Most guys would be glued there right now. Ok, what would you change?"

"Nothing, I really like your tits," I said, turning even redder, if that were possible.

"Thanks, so do I. There's definitely something there to attract attention, but not too much. What about the butt? Do you like big butts?"

"Not really."

"What about legs?"

"Long, with a good muscle structure."

"Great. Now, here is what you just told me is your ideal woman; 5'9" or 5'10" tall, long, straight red hair, green eyes, an athletic build, long muscular legs leading up to a nice tight butt. Is that an accurate description?"

"Yes, that would be correct."

"And you still don't see it do you?"

"I guess not. See what?"

"You just perfectly described Jenny Adams."

I sat there for a moment. She was right of course, but I had never made the connection.

"Did you know that most guys think Jenny is the best looking girl in school? Many also think you are an idiot for not dating her. You've been best friends for so long you two cannot see it any other way. You should start looking at Jenny as the beautiful woman she is. With the great friendship you've already built, you two would make a perfect couple. Think about it, you dope," Anne ordered with a grin.

"I will, I promise," I said. "Now, I'd better get you home before your dad sends out the posse."

I drove her home in silence. When I walked her to the door, I said, "Thanks a lot for telling me that, Anne. I guess it's true it's sometimes hard to see what is right in front of your nose."

"You're welcome. I'm sure you two will be very happy together. Now, I don't usually do this on a first date, but as I'm pretty sure I've just ensured there won't be a second one, kiss me good night."

"Gladly."

I leaned forward and gave her a gentle kiss. She was having none of that. Throwing her arms around my neck she pulled me in for a nice, hard kiss. It seemed to last forever, breaking only when we ran out of air.

"Thanks, that's just what I wanted," she said smiling. "Now, go get her, Tiger!" With that, she turned and went inside.

It's a good thing the route home was so familiar, as I was not paying too much attention to where I was going; I was thinking about Jenny. She was beautiful. She was also a great person. She was funny and fun to be around; kind to everyone; caring with genuine compassion; helpful whenever you needed her. She had so many wonderful qualities that it's hard to think of them all.

Two days later, Jenny was over at my house watching TV. As the movie ended, she turned to me, saying, "Okay, Tony, what's up? You've been quiet all day and you've been giving me some funny looks."

I hesitated before answering, unsure as to how to answer. I was really nervous about how this would go. I took a deep breath.

"Jenny, will you go out with me on Friday?" I asked her.

"Sure, we can get together and..."

"No, please, that's not what I mean. I don't want to just get together; I want to go on a date, a real date."

She looked at me with her eyebrows raised. I could see the wonder in her eyes.

"Look, Jenny, I know we've been friends for a long time, you've always been my best friend, but lately I've been seeing you in a different light. I've always known you were pretty, but I'm starting to see just how beautiful you really are. I've always known you were a girl, but now I'm seeing you as a woman. We're friends but I'd like to see if maybe we could be more."

She sat there, deep in thought. I waited for her to decide.

After several minutes I added, "I know this is sudden. You don't have to answer now if you want to think about it for a while. Don't be afraid to say no. Nothing will change if you say no."

She smiled at me and said, "I don't need to wait. Of course I'll go on a date with you. I just wasn't expecting it. What brought this about?"

"I'll tell you, I promise, but not right now. What time do you want to start?"

"Um, I'll let you know."

"Fine. Want a Coke?"

"Sure."

I went a got one for each of us. We watched some more TV, neither one of us talking much. When she left to go home, she paused at the door and gave me a long look, smiling slightly.

The rest of the week seemed to last forever. Jenny must have said something to her dad, and he spoke to my parents, because on Wednesday evening Mom came into my room, announcing, "Let me know what you plan on wearing for your big date Friday, and I'll make sure it's clean and nicely pressed."

"Okay, Mom, thanks. I'm not sure...wait, how did you know about Friday?"

"Moms just know," she said, grinning. "If there's anything else I can do for you, let me know."

When Friday came, I had still not told her what I wanted to wear, having changed my mind several times. I went out in the afternoon to get a haircut. When I got back home, there was a brand new outfit laying on my bed waiting. It was perfect. As I was getting ready, my dad came in my room.

"Here, try some of this," he said, handing me a bottle of cologne. "It's a very popular scent."

"Thanks, Dad."

"Also, a good date needs a good ride. Take my car tonight."

I was stunned. Dad rarely let's anyone drive his car. He had saved for years to afford it. "Are you sure?" I asked.

"Yes, I'm sure. I got it cleaned up nicely today and it's got a full tank of gas. Enjoy yourself."

"Wow, thanks, Dad! You're awesome."

When the time came, I walked across to her house and knocked. Mr. Adams answered.

"Come on in Tony, she'll be right down. Where are you going tonight?" he asked.

"I made a reservation at that new Italian place south of the mall. After that, we'll just see. Probably a movie later on," I answered.

We heard the sound of Jenny coming down the stairs. I turned to see her and was stunned. She was wearing a light green sun dress that stopped just above her knees. Her legs looked great, tapering to a pair of strappy sandals with a 2½-inch heel. Her red hair cascaded down over the front of her shoulders, framing her face nicely. Jenny's eyes were sparkling and she was grinning from ear to ear.

I walked up to her as she got to the bottom of the stairs.

"I've never seen you look more beautiful," I said.

She blushed a little and said, "Thanks, you look great, too."

We walked back to her dad.

"Have fun tonight you two," he said. "I've talked to your parents, Tony, and for tonight, and tonight only, there is no curfew for you two - just don't push it too far."

"We won't, Mr. Adams, I promise," I said.

We walked across the street to the car. Jenny's eyes got huge when she saw we were heading to Dad's car. We drove to the restaurant in an awkward silence. As we were waiting for the table, I reached out and took her hand in mine. I wasn't sure if it was a good idea, as I figured she could feel that my heart was beating about 200 times a minute. Jenny just smiled at me and squeezed it gently.

Dinner went well. The talking started slow, but we loosened up some as things went on. By the end I think I had my heart down to about 150.

As we walked back to the car, I took her hand again. Before I opened her door, I turned her to face me. "Are you still as nervous as I am?" I asked.

"Oh God, yes," she replied.

"I have an idea, but I don't want to make it worse," I said quietly.

She looked up at me, whispering, "I don't think anything would make it worse."

I leaned forward and kissed her. As our lips met, it felt like I had touched 1,000 volts. The excitement went from head to toe. I wrapped my arms around her, pulling her to me gently. Jenny hesitated for a moment, and then just melted in my arms.

After several minutes, we broke the kiss. Jenny was smiling broadly and looking at me dreamily.

"Now we don't have to worry about That for the rest of the night. One less thing to think about," I said.

She just started laughing, pulled me in and hugged me tightly. I could feel all the tension leave her body. She felt so good in my arms; I knew I wanted this to happen a lot more.

After a few minutes, she pulled back, looked at me and said, "You're right, I was thinking about it. I shouldn't be bothered about it anymore. I do think, however, that we should make sure."

She leaned in and kissed me again. This one was even better because we were both putting more of ourselves into it. She kept holding me tighter and pulling me closer, her hands pressed to the back of my shoulders. I put one hand on her lower back, gently rubbing. With the other hand I reached up and held the back of her head, my fingers entwined in her hair. The feel of her tits pressing against my chest aroused me and I began to stir in my pants.

We finally broke the kiss when we heard a whistle from near the restaurant. I turned to look and saw a couple standing there. He was looking at us and she was tugging on his arm to get him to move. When he saw us staring back at him, he gave in and they walked off.

I turned back to Jenny, worried she'd been upset by the scene. "Maybe we should go somewhere else."

Jenny and I decided to go over to the theatre, where we quickly agreed on a movie. We sat in the back, with my arm around her and her head resting on my shoulder. I enjoyed the feeling of her up against me so much that I wasn't paying attention, and still don't remember what movie we saw.

Afterward, we went down to the park on the waterfront and just walked around holding hands. Finally, around 12:30 a.m., we decided we should get home. Standing on her porch, I looked at her and couldn't help but smile.

"I have never had a better night in all my life," I said.

"Me neither. I'm just upset we waited so long to do this," she said.

"I know, we were kind of dumb, weren't we?"

"We'll just have to do whatever we can to catch up." Jenny winked.

We stood there kissing for about twenty minutes. I decided I should be getting home before her dad came to investigate. I was a little surprised he hadn't yet.

I don't think I touched the ground as I went across the street. It took me hours to fall asleep; I didn't want the night to end and went over every detail, committing each to memory.

For the rest of the summer, except for the five days Jenny and her dad were at her grandparents, we spent every day together. We got closer and closer. At one point when we were at the mall, we ran into Anne, who noticed we were holding hands. She told us she was very happy for us. I confessed to Jenny that it was Anne who had suggested that I look at her closer. Jenny gave Anne a big hug and thanked her profusely.

When school started, it quickly got around that our friendship had blossomed into romance. It seemed to be the general consensus that this was a good thing. We got a couple of grumbles from a guy who had been after Jenny to go out with him since our freshman year, but we just ignored him.

Every day after school we did our homework together, helping each other through troublesome concepts. It may have taken a little longer than if we had done it separately, but we didn't care because we were enjoying every minute of it.

I once overheard my dad talking about us to my mom, saying, "We haven't spent as much time as they have together since we were on our honeymoon!" Mom just told him to mind his business and leave us alone.

The Second Nudge

It was March and Mr. Adams was leaving on a business trip. We had celebrated my 18th birthday the night before and we were all still in a good mood, or so I thought. My parents and I walked across the street to Jenny's house. They were going to drive him to the airport while I stayed with Jenny. Mr. Adams greeted us at the door and let us in.

"Where's Jenny?" I asked, not seeing her there.

"She's up in her room right now," he replied. "Listen Tony, I need to talk to you for a moment before you see her. She's a little upset right now."

"I thought something was bothering her, but she said it was nothing"

"It started a couple of days ago when she got the mail. There was a letter addressed to her mother, from her high school reunion committee. I wrote them last time to say she had passed, but I guess they never put that down on their records. It got Jenny thinking about her."

Jenny has told me many times how much she misses her mom. My mom has been a great help to her as sh