the Table61 blog

Jessie’s Boys: Chapter 3

by on Sep.06, 2009, under 'The Blog'

“You’re not wearing that are you?”

“It’s my good luck charm.” Well, it was supposed to be.

Stewart was referring to the little black dress, size 2.

Jessie had been good friends with Stewart in high school, but they had lost touch when she left for college. She had recognized him at the bookstore. He was carrying a hiking magazine.

“You like the outdoors?”

“Ya, I love hiking and rock climbing. In fact, if I was taking a girl on a date, that’s what I’d do with her. So much better than dinner and a movie.”

“That sounds like fun. You’re right, something different would be nice for a change.”

Stewart glanced down at the book Jessie was carrying; “Advanced Techniques of Kama Sutra.”

“Oh my god, no, this isn’t mine. It’s my sister’s. I’m holding it for her until she gets out of the restroom.” Jessie was blushing, scared he didn’t believe her. “I haven’t even had sex in like a year.” Jessie paused again, embarrassed at what she’d just said.

“So you’re single? How would you like to join me for a hike this weekend?” Jessie accepted, and her sister walked over to them, taking her book. She looked at Stewart, smiling.

“Who’s your friend?”

“My date for this weekend.”

“Damn. I hoped I’d get a chance to try this soon,” she said while thumbing through the book. While Jessie was embarrassed by her sister’s promiscuous behavior, at least Stewart should believe the book wasn’t hers.

On Saturday, Jessie had decided she wanted to drive, having had a few bad experiences recently.

“Well, I’d let you, but we need my truck to get to the hiking trail. I really think you should change out of your dress, or at least take a jacket.” Jessie refused. Stewart gave up; at least she had on suitable shoes.

Stewart picked an easy three mile trail. He had really wanted to do Trail 7, but that involved a bit of rock climbing, and he was sure Jessie wouldn’t want to do that in her dress. They set off, and Jessie seemed to easily keep up. About halfway through he stopped them near a small stream and took off his back pack.

“I should have clarified; I don’t think the whole dinner for a date thing is lame; just when its in a restaurant.” He pulled out a small picnic set and some food. Jessie was incredibly impressed. This was about the most romantic thing anyone had ever done for her. He had even brought a small bottle of wine. They sat on the ground and ate. Jessie was so glad her little black dress was starting to bring her luck, even though it was getting a little dirty.

“So it sounds like you haven’t had a boyfriend in a while. Bad luck with guys?”

“Ya, I seem to pick some real losers. I’ve gone on a few dates, but they’ve been disasters. I don’t even want to talk about it. How about you?”

“Well, a few weeks ago my girlfriend broke up with me. I should have seen it coming. She’s been with a lot of guys in the last year. I just thought I’d be different. She was with The Next Guy within two days.”

“Ouch, that sucks. Especially since you seem to be such a nice guy.”

Stewart smiled at her, and then laid back and stared at the sky.

“Uh oh… I forgot to check the weather for today. It looks like it may rain soon.”

Jessie offered to help, “Well, I can check it on my phone.”

“Not likely. You can’t get cell reception out here. Got to head about five miles back up the road. We’re pretty much completely alone. In fact, I’ve only seen one other person out here ever. We’d probably get moving so we don’t get stuck in this rain.”

They packed up and continued on their hike, talking the whole way. “I hope you liked the wine. I didn’t even think to ask whether you drank alcohol.”

“Ya, I’m a social drinker. I don’t really get drunk that often though.”

“Oh, that’s about every night for me. I pass out a lot, and wake up in bed with girls I don’t know. Luckily, Gabe taught me a great trick. I ask them what their middle name is, and then say ‘Well from now on I’m gonna call you that.’ It saves a lot of embarrassment.”

Jessie was a little shocked that he’d share this, but decided to play along. “Megan.”


“Megan. That’s my middle name. Now you have no excuse to forget my name.”

“No, I guess I’ll have to be careful. But that’s my ex-girlfriends name, so at least I won’t get in trouble if I mistake you.”

“Well, then how about we just ban you from ever calling me by my middle name.”

“Sounds fair.” Damn. He realized that he should have just kept his mouth shut.

It started sprinkling when they were about fifty feet from the truck. “Wow, we got here just in….” He stopped talking, hands digging through his pocket. “Umm… I must have dropped my keys when I pulled my knife out to open the wine. I’ll run back there real fast. Well, maybe not real fast. Three miles should take me about twenty five minutes. Do you just want to wait here? I should be faster without you.”

“Alone in the woods? I think I’d rather do another three miles.”

Within minutes, it had started pouring. Jessie was immediately soaked and cold. Luckily Stewart was able to put her phone in his pack to keep it dry. It was pretty useless out here anyway.

They returned to the picnic spot without any further conversation. The first words out of Stewart’s mouth were “oh no.”


“Do you remember where we sat.”

“Ya, right along the stream around….” She stopped, noticing the problem. The small stream was no longer small. The place they had been sitting was now covered in fast flowing water. The keys were gone.

They walked back to the truck. Stewart opened the door and started putting his pack inside.

“Wait a second, the doors were unlocked. Why didn’t you tell me that. I could have been here warm and dry. Instead, I have nipples about to poke holes in my dress.”

Stewart smiled, even though she was yelling. “Ya, I noticed. Sorry about that.” She got in the truck and dug through his pack to get her phone, but he was right, no bars. She screamed again. Stewart climbed in the truck and suggested that he could walk up the road until he got signal and call someone to pick them up. An hour later, he returned.

“Ok, we should have a ride soon. My buddy Mitch is going to come pick us up, and I’ll just have to find my spare key at home tonight.”

Mitch arrived soon, and Jessie was glad to climb into a warm truck, although now she had two guys staring at her frigid chest. She was debating whether she was going to give Stewart another chance.

Mitch started teasing. “Why is it that on your date I have to pick you up in my truck. Doesn’t seem very manly.”

“Oh, stop your bitching. I tell you what, I’ll be a gentleman and pay you back. We can have Jessie hook you up with her sister. She’s even hotter and seems pretty kinky.”

“Sounds good to me.” As Mitch laughed, Stewart realized what he’d just said. He looked at Jessie.

“Don’t get me wrong, your pretty too. I just happened to ask you out before I met your sister.”

“Dude, not smooth,” Mitch warned his buddy.

Jessie made up her decision. There wouldn’t be a second date.

Jessie walked into her house, alone. Her sister looked at her and could tell things had gone poorly. “Get stuck in the rain?”

Jessie felt like being a wise-ass. “Actually, no, we were inside for all of that storm. We got kind of intimate and he poured a bottle of champagne over me.”

Her sister’s eyes lit up. “Really? That’s like rap video stuff. That’s awesome. Good thing you wore that dress huh. I told you it was good luck.”

Jessie continued on the way to her room, muttering to herself, “No, good luck would have been if I had been the one in the restroom.”

“Wait, so are you going back out with him?”

“No, we just didn’t click.”

“Ok, good, because I found out that Craigslist has personals, and I thought about setting you up on a blind date. Actually, I thought we could double date.”

Jessie actually liked this idea. Maybe an extra couple would make things smoother… Or maybe it would be double disaster.

Before closing her door, Jessie heard her sister yell one last thing.

“By the way, you should really start wearing a bra with that dress.”

— This story, at least the first half, based on how I want to take a girl out. The second half is about how I figure it would actually turn out.

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