Ted and Rachel Derwin-Finkel’s first date and first kiss mark Ted’s awkward entry into romantic experience—and expose the gap between his private intentions and the relationship Rachel believes they are beginning. At seventeen, he asks her out without being attracted to her, partly because he has never held a girl’s hand and partly because he hopes dating her might improve his chances with Anna Travis. The evening he imagines as a brief experiment instead ends with Rachel kissing him, teaching him how to kiss, and becoming his girlfriend for the next four months.

Background and Unequal Expectations

Ted asks Rachel out after tutoring, stumbling through the invitation and regretting it as soon as he has spoken. Rachel responds by taking charge: she gets his phone number, gives him hers, specifies when he should call, and, when he does, lays out the film, its screening time, and where they will eat beforehand. She even explains how to reach her house so he can pick her up. The date is organized around her clear interest and initiative, while Ted’s invitation has been shaped by motives he does not share with her.

His interest in Anna is central to that imbalance. Ted reasons that dating Rachel might help his prospects with Anna, imagining that Anna could recognize her feelings if she saw him fall for someone else. He also entertains the possibility that his own feelings for Rachel might develop, though he is not attracted to her. At seventeen, with no experience holding hands, he treats dating as both an opportunity to learn and a tactic in a different, unspoken pursuit. Rachel, by contrast, behaves as if a first date can naturally lead to more: after the cinema, she talks rapidly about another outing, a new Thai restaurant on Seventh, a romantic comedy they should see, and a Halloween costume group she and her friends are forming. She welcomes him into plans that Ted has not decided he wants to share.

The Date and Ted’s Attempt to End It

Ted experiences the evening as something Rachel has arranged and inhabited without him. He cannot quite identify who he has been on the date with; it does not feel like himself. In his private assessment, Rachel could have taken an inflatable doll to the cinema and enjoyed herself just as much. The image conveys more than awkwardness: Ted feels that he has contributed nothing, even as Rachel’s talk of future plans assumes their participation together.

On the drive to her house, he decides to clarify that there will be no second date. He expects Rachel to hate him and considers withdrawing from the tutoring program, but thinks that avoiding future encounters might be worth the embarrassment. Yet he has not worked out how to end things directly. He wonders whether one date obliges him to explicitly break off contact, or whether he can stop tutoring her and let her understand the hint. When they arrive, he parks without turning off the engine, a small practical detail that sits uneasily beside Rachel’s expectation of a goodnight. She unbuckles her seat belt and says goodnight but does not get out. Ted answers and leans across to hug her, patting her back delicately in the hope that the gesture will communicate an apology and a plea not to resent him.

The First Kiss

Instead of accepting the hug as an ending, Rachel puts her hands on Ted’s cheeks, holds his face still, and kisses him on the mouth. For Ted, the shock of his first kiss momentarily drives every other thought away. He freezes, his jaw slack, while Rachel moves her tongue around his mouth. When his mind catches up with his body and reminds him that he is supposed to kiss back, Rachel has already pulled away. She covers his lips with smaller kisses and shows him how to continue, apparently recognizing that he does not know where to begin.

The instruction humiliates him. Ted has just planned to reject Rachel, yet now feels exposed as inexperienced while she takes the lead in both the kiss and its interpretation. After a few minutes, though, he finds that kissing is not difficult. It is not the thrilling experience he had expected: Rachel’s glasses keep knocking against his nose, and seeing her so close makes her seem almost like an indistinct painting. He tries closing his eyes but feels uneasy, as if someone might come up behind him. His attention fixes on the physical awkwardness—the closeness, the glasses, and the popcorn smell on her breath, which he cannot determine might be his own. He wonders whether he would have enjoyed the kiss more with Anna, but cannot even imagine becoming aroused by kissing. Rachel seems much more absorbed, sighing and moving against him, while Ted remains caught between curiosity, discomfort, and shame at his own inexperience.

Aftermath and Retrospective Meaning

The date does not end with Ted’s intended refusal. He and Rachel see each other for the following four months. That outcome makes the evening a reversal: Ted arrives with an ulterior hope involving Anna and a plan to avoid a second date, while Rachel’s initiative turns the night into the beginning of a sustained relationship. His first kiss is not a triumphant romantic revelation. It is startling, awkward, and only partly pleasurable, and its importance lies as much in how little Ted understands his own participation as in the milestone itself.

Looking back, Ted identifies Rachel as the first woman who could plausibly accuse him of treating her badly. He distinguishes his conduct toward her from his earlier behavior toward Anna: with Anna, he believes he acted cowardly by concealing his feelings, but also tried to be kind. His recollection of Rachel carries a sharper sense of culpability. That later judgment gives the first date an uneasy retrospect: Ted’s failure to share his actual intentions is present from the start, even though the scene’s immediate drama is his first kiss and his embarrassment at being taught. The four months that follow make the date more than an isolated adolescent mishap, but the account does not turn the kiss itself into a simple promise of romance.