The day after my disaster date with Franco, Lenny is on damage control, dutifully dragging me out of my bedroom to join her at our local coffee shop. It's just past sunset and the sky's pale color almost matches the underside of my arm, so I'm staring at the pale wispy clouds on the horizon wondering when the stars will come out.

"Silvia, I took you out for a reason. I wasn't planning to watch you stare at the sky all night," Lenny catches my attention with her sour expression. She nudges the steaming cup of chai tea in front of me forward more.

"Sorry," I respond sheepishly, taking the proffered cup of sweet tea with a grateful smile.

"So, the date when badly?" Lenny asks while I'm sipping at my drink. The liquid's too hot and I feel the tip of my tongue burn, so I set the drink down with a sigh.

"There was nothing wrong with the date," I tell Lenny, pausing to gather my thoughts. "The restaurant was suitable, the timing was perfect, and the dessert was delicious. Franco and I just couldn't make a connection."

"But you're at the very least attracted to him right? I mean, why else would you go out with him in the first place?" Lenny asks.

"Well, he's attractive, I guess. He has a good job, a nice car, a college education, and an adorable cocker spaniel named Doodles."

"So when he asked you out, your first thought was 'sure, that guy has a nice dog'?" Lenny asks me with an incredulous look.

"No, though it did cross my mind," I respond to bait Lenny a little. She rolls her eyes and then takes a big swig of her iced coffee. With a sullen sigh, I turn my attention to my drink in my hands.

"You know what the problem is?" Lenny asks.

"No, tell me," I respond without pause before Lenny can continue. Because she's used to my sarcasm and fluctuating moods, she ignores my comment and looks thoughtfully at me across the table.

"The problem is you don't know what you want. You know what you're supposed to want when it comes to a guy, but you haven't been testing the waters enough to know your type," Lenny says.

I scoff a little at Lenny's theory, but don't say anything. Instead, she continues to elaborate while I contemplate burning my tongue again with the delicious chai tea.

"Think about it. You've been dating for almost three years now, and only really had two serious boyfriends. In between Kelvin and Riley, you've struck out with a handful of guys, all because you never really connected with them," Lenny tells me with an intense look that means she's on a roll.

I open my mouth to intervene, but she shakes her head and holds up a hand to shush me. With a slight frown, I close my mouth and wait for her to finish.

"You just haven't found your type yet because, as per usual, you're too wrapped up in everyone else's opinions to form your own," Lenny concludes, looking very much satisfied with herself.

"If that's true, then following your advice will only continue the cycle," I point out cheekily. Lenny waves off the comment with an easy smile.

"My opinion matters because I'm your best friend. You'd be crazy to ignore what I'm saying," Lenny tells me. "I know you better than yourself sometimes."

"Mmm," I respond skeptically. She gives me a stern look, and I try to hide behind my coffee cup when I drink from my chai.

"Shit!" I curse, putting the cup down not long after picking up. "I forgot the tea's still hot."

"Mmm," Lenny's response mirrors my own earlier.

"Can I have a sip of your iced coffee?" I ask Lenny, already reaching across the table for it. Lenny takes it just out of my reach, teasing me with it.

"Only if you admit I'm right," she says in a singsong voice.

"Fine, you're right," I tell her, still grasping after the icy drink.

"About?" she asks, keeping the drink mere inches from my fingertips.

"About the fact I need to find out what I'm looking for in my potential mates. Now give me the coffee, my tongue is throbbing!" I exclaim with a huff. Lenny hands me her drink with a triumphant grin.

"There, that wasn't so bad, now was it?" she asks. I choose not to respond, drinking a good portion of her drink instead.

"Now, let's try to think about the qualities you liked about both Kelvin and Riley. Even if you don't have a type yet, you obviously can recognize qualities that attract you to a guy," Lenny suggests.

I frown while I consider my two previous relationships.

My first boyfriend had been Kelvin, a sweet but somewhat conceited senior I met during my first year of college. Most of our time together was spent at the local arcade or watching movies in his bedroom. Kelvin never really introduced me to his family or friends, and preferred not to interact with my own family and friends. Our relationship naturally fell apart after summer, when Kelvin moved away for medical school, and I spent more time at school and work.

Some five months later, I met Riley at a single's mixer for Valentine's Day. Riley was a personal trainer at a local gym, who loved to be unpredictable and adventurous. During our relationship, our dates varied from hikes along the beach, to surfing lessons by the pier, and late night cooking lessons from his Italian grandmother. Then one day, Riley told me he was making plans to go backpacking across Europe for six months, which pretty much ended the relationship.

"You know there's not much in common between Riley and Kelvin, right?" I point out to Lenny. She shrugs a little.

"Maybe it's the few things that they did have in common that you liked about them."

"Good point. I guess one quality that they both shared was motivation. Kelvin worked hard to make it to medical school, and Riley loved to challenge himself with marathons and weight lifting."

"Alright, what else?" Lenny encourages me.

"Well, Riley and Kelvin were both at least three or four years older than me. They both were a bit more mature because of their age, which I liked," I respond.

"So you're into older men, it's understandable," Lenny says, nodding her head.

"If you think about it, they have more experience, and more experience translates to better romance. Both of them knew how to kiss well, that's for sure," I tell Lenny. She laughs.

"So far, your type seems to be older, motivated men who know how to charm a lady and play tonsil hockey well," Lenny lists off.

"That doesn't seem very specific," I tell Lenny thoughtfully. "That description fits a lot of people."

"Oh? So you'd say that describes Franco?" Lenny asks me.

I frown. "No, I guess not. Franco's younger than me, and even if he was charming enough, he's only got an associate's degree. He's not even sure what he wants to do with it."

"So Franco doesn't fit your type, because he's not old enough or motivated, thus why you two didn't connect," Lenny tells me.

"But saying I'm looking for an older, motivated and charming man might limit me to dating the wrong men, don't you think? I mean, what if the perfect guy for me is our age, laid back, and goofy? If I listen to your advice, I wouldn't give that guy a chance."

"It's just a guideline Sil, not the law. If you find that guy, and you like him, then go for it. I won't stop you, but I will say I'd be surprised," Lenny responds, quelling my growing annoyance.

"Fine," I respond with a deflated sigh.

"So, who can you think of that is an older, motivated, and charming single man?" Lenny asks.

"Aside from Riley and Kelvin? I don't know, maybe your brother?" I respond.

"Connor?" Lenny scoffs, "You're kidding, right?"

"Well, he is older than me, he's a partner in Theo's business, he's an amazing PR consultant, and who's more charming than Connor?" I list off to Lenny, mostly to watch her expression as it sours. She's glaring at me as I finish.

"Anyone is more charming than my brother," Lenny deadpans. "He's the epitome of evil. He cut the heads off my Barbie dolls when I was in first grade. He spread rumors about me sniffing glue in middle school. He punched Harrison Lee in the face right after our first kiss. He moved into the flat above mine when I moved out last year. On top of that, he's got a very ugly flower tattooed on his ankle."

"He's got a tattoo?" I ask with piqued interest.

"You're missing the point!" Lenny exclaims, "My brother is not your type. He's single for a reason, that reason being he will never find a woman crazy enough to stay in a relationship with him."

"He can't be that bad," I tell her.

"Say what you will, it won't change the past," Lenny responds stubbornly.

"I have fond memories of your brother. He made us pancakes the night after prom, and covered for us the morning after we came home at three in the morning, still drunk from tequila shots with Sheila and Connie."

"He also hid the aspirin from us the morning after, when we both learned what it felt like to have a hangover," Lenny informs me with a pointed look.

"Oh," I say. "I didn't remember that part."

"It doesn't matter really, Connor's off limits either way. He's my brother, and you're not allowed to date my brother." Lenny looks at me sternly.

I shrug and finally give in to her objections. "Fine, do you have anyone else in mind?"

"As a matter of fact, I do," Lenny says with a sly smile. I assume the statement is ominous and foreboding because Lenny looks determined and lost in thought. She begins rapid-fire texting without saying much else to me, so I nurse my chai tea and ponder the consequences of my decision.

Allowing Lenny to play matchmaker feels like letting a pyromaniac play with fire. I'll just have to wait and see if it will blow up in my face.

A/N: Chapter edited 8/1/12. Minor changes mostly to the dialogue. All readers and reviews are appreciated. Thank you!