So Jesse's talking to Dawnie and Sam on the phone. "You are not going to believe this," she says, and off we go to the Land Of Voice-Over Flashback. "We meet for morning coffee," says Jesse, while Flashback-Cam shows Jesse and some guy meeting for coffee, "and I am looking HOT in my new eggshell Donna Karan sweater." Flashback-Cam shows her looking not all that HOT, maybe because the effect of the sweater is overshadowed by yet another cantilevered up-do, which I shall call "Fantasia With Descending Eels." Anyway, Jesse describes the guy she's with: "Coffee Boy is dressed entirely in black, as usual every bit the handsome brooding romantic genius," which, as we see, pretty much translates into "guy with blank expression." We learn that Jesse has met this guy six times for coffee and he hasn't made a move -- she insists that "he's shy." The way the Flashback-Cam circles around and around the table, you'd think it was strapped to a buzzard with a taste for only the most pretentious carrion. We see Jesse is peeking demurely at Coffee Boy through the many dozen "face-framing tendrils" that have sprung forth from her 'do. Her voice-over continues, "Today, he finally made a move of some kind," and we see that he reaches across the table to caress her face, though she says she's not sure he wasn't brushing off some muffin crumbs, and I'm not sure he wasn't saving her from swallowing a big hank of her own hair. Anyway. Jesse keeps saying to Sam and Dawnie that she's sick of making the first move: "From now on I will be demure and soft and coy and subtle," and from Flashback-Cam we see that this entails her reaching over and caressing Coffee Boy's thigh, and I guess she means "subtle" as in using one finger to stroke his thigh instead of her WHOLE HAND. Coffee Boy is so startled that he dumps his coffee all over Jesse's DKNY-clad chest. Ouch! That's gotta hurt, Donna.
Flashback over. Back in the present, Jesse is screaming on her cell phone in the bathroom stall, with the big coffee stain still on her front. She should be calling her dry cleaner, but she's still talking to Dawnie and Sam. "I have NO idea how to be SUBTLE!" she wails. Yeah, Jesse, well, it helps to start with not screaming. ["And to think these words were put into her mouth by Kevin Williamson . . . " -- Sars] She goes into this long rant about how she is going crazy, is addicted to double cappuccinos, has second-degree breast burns, "and still I have no idea how [Coffee Boy] feels!" Well, sensitive in the thigh area, obviously. "What the hell do I do?" she asks her friends. "Switch to decaf," says Dawnie. "Yeah, definitely decaf," says Sam. They snicker and hang up. Jesse emits furious, strangled screeches of rage. And my mouth is open, but no sound, no sound comes out at all.
Jesse's at work, doin' some promotin'. She meets with a client, an older guy, who tells her, "The way I see it, yours is an entire generation that's lost its way." It hasn't lost its way nearly as profoundly as Jesse's topknot, but whatever. Client Guy goes on to say that "whenever a generation loses its way, there's money to be made helping them find it again." Ha, ha! I get it! Can I see some more commercials? Client Guy says he believes that with Jesse's help, "High Hopes Courting Encounters can be the answer." Jesse says that "dating services are currently about as hip as fluorescent pink rhinestone-encrusted 1980s-style ripped Flashdance sweatshirts." As opposed to, say, eggshell Donna Karan sweaters with big old coffee stains on them. Nevertheless, Client Guy is all into the concept for his High Hopes company, saying the service can teach people how to date again. "You are the demographic that we are after," he says to Jesse. "Disconnected. Lonely. Neurotic. Unattached. Approaching thirty. Feeling hopeless." Jesse's like, "Shut up." Client Guy says that they can make High Hopes hip again, with some hype.