After the tennis game, Alvy and Annie have an awkward, nervous, exploratory conversation, trying to strike up an acquaintance. In her balletic performance, Annie's endearing, stumbling, flailing gestures reveal her zany, yet huggable nature. They both make self-conscious, shyly banal, but believable statements to each other (particularly her self-effacing "La-dee-dah. La-la. Yeah") and she clumsily asks him if he wants a ride home:

Annie: Hi, hi, hi.
Alvy: Oh hi, hi.
Annie: Well, bye.
Alvy: You play very well.
Annie: Oh, yeah. So do you. Oh, God, what a, what a dumb thing to say. Right, I mean, you say, 'You play well.' So right away I had to say, 'You play well.' Oh, oh God Annie. Well. Oh well. La-dee-dah. La-dee-dah. La-la. Yeah.
Alvy: You want a lift?
Annie: Oh, why? Uh, you got a car?
Alvy: No, I was going to take a cab.
Annie: Oh, no. I have a car.
Alvy: You have a car? I don't understand. If you have a car, so then why did you say, 'Do you have a car?' like you wanted a lift?
Annie: I don't, I don't, geez, I don't know. I wasn't....I got this VW out there. (to herself) What a jerk, yeah. Would you like a lift?
Alvy: Sure. Which way you goin'?
Annie: Me? Oh, downtown.
Alvy: Down.... I'm going uptown.
Annie: Oh well, you know I'm going uptown too.
Alvy: You just said you were going downtown.
Annie: Yeah, well, but I could...

On the wild drive which barely misses multiple collisions in her open VW Beetle convertible, Alvy first learns that Annie is an aspiring singer/actress and a middle-class WASP from Chippewa Falls, Wisconsin. Alvy explains why he doesn't drive even though he has a driver's license: "I got a license but I have too much hostility." Getting out of Annie's badly parked car, Alvy says:

That's OK, we can walk to the curb from here.

Alvy compliments Annie's kookiness with a mouthful of non-sequitur praise:

You're a wonderful tennis player...You're the worst driver I've ever seen in my life...and I love what you're wearing.

Naively innocent, Annie explains that her tie was given to her by Grammy Hall. Alvy wonders about Annie's Midwestern background:

What did you do? Grow up in a Norman Rockwell painting? Your Grammy?

Alvy bitterly jokes about his own background as an intellectual New York Jew (with more Jewish paranoia), whose grandparents, Jewish Russian peasants, had a hard life: "My grammy never gave gifts, you know. She was too busy getting raped by Cossacks."

Alvy is invited upstairs to Annie's apartment for a glass of wine. He has nothing scheduled until his psychoanalyst's appointment, a therapist he has been seeing for fifteen years: "I'm gonna give him one more year and then I'm going to Lourdes." Alvy notices her recent reading material, Sylvia Plath's book Ariel: "Interesting poetess whose tragic suicide was misinterpreted as romantic by the college-girl mentality." Annie responds gauchely as a hick-midwesterner: "Some of her poems seem neat." Annie shows him pictures of her family on the wall, including her brother Duane and Grammy Hall.

In an emotionally uncertain and vague tone, the flaky and rambling Annie speaks of death in an amusing but morbidly "terrible" story of Grammy's brother - George, a "shell-shocked" veteran from World War I, died in a fit of narcolepsy while standing in line for his free war-veterans' turkey. The wacky, anecdotal story about death leaves Annie feeling confused and wondering why she even told the story in the first place.

As they move to the outdoor balcony to get better acquainted, Alvy believes he is all "perspired," because he didn't clean up in the sports club. "I never shower in a public place," he explains, "'cause I don't like to get naked in front of another man...I don't like to show my body to a man of my gender. You never know what's gonna happen." Before their relationship takes off, Annie makes a bizarre comment to Alvy, igniting more of his anti-Jewish fears:

Annie: Well, you are what Grammy Hall would call a 'real Jew.'
Alvy: (startled) Thank you.
Annie: Yeah, well, she hates Jews. She thinks they just make money, but let me tell ya, I mean, she's the one. Is she ever, I'm tellin' ya.

In the memorable subtitle scene on the balcony off Annie's apartment with a cityscape in the background, their real thoughts are seen in thought-bubble subtitles (like from exotic foreign films) at the bottom of the screen as they carry on absurd, small-talk banalities in their conversation about photography. Their budding sexual attraction, exciting interest in each other, and courtship are beautifully evoked:

Annie is obviously feeling that she lacks self-confidence and is intellectually inadequate, yet unconstrained by proper vocabulary when she comments on "aesthetic criteria" -"You mean whether it's a good photo or not?" She thinks to herself: "I'm not smart enough for him. Hang in there." The thoughts in the subtitles are more believable than their words:

Alvy asks her out for a weekend date, and ends up accompanying aspiring singer Annie to a Saturday nightclub audition for their first date. [The scene was filmed at the Grand Finale nightclub.] They share similar sympathies about stagefright and performing in front of an audience. It is an inauspicious beginning for Annie's career that will ultimately lead to her independence as a "Singer" and the breakup of their relationship. Microphone feedback, the loud crash of dropped plates, a ringing telephone, uninterested oblivious patrons, and other audience distractions make it an awful debut experience. Photographed from a distance and seen as a small figure in the background, she timidly sings "It Had To Be You" - it marks the symbolic start of their relationship.

Walking along on the sidewalk afterwards, Alvy attempts to make her feel better, encouraging her as an older mentor: "The audience was a tad restless...You have a wonderful voice." Suddenly he stops and asks for a kiss so they won't have to be tense all evening:

Hey, listen, listen. Give me a kiss....Yeah, why not? Because we're just gonna go home later, right, and uhm, there's gonna be all that tension, you know. We've never kissed before. And I'll never know when to make the right move or anything. So we'll kiss now and get it over with, and then we'll go eat. Okay? We'll digest our food better.

At dinner in a Jewish delicatessen where Annie feels out of place, she orders a WASP-ish meal with no idea of how to order 'properly' in a deli - pastrami on white bread "with mayonnaise, tomatoes, and lettuce." Alvy grimaces, and then talks about how his second wife left him, "nothing that a few megavitamins couldn't cure." His first marriage to Allison didn't work because "it was my fault. I was too crazy," Alvy admits.

Suddenly, Annie and Alvy are in bed and have just finished making love. They have come together despite their ethnic and personality differences. Alvy theorizes how sex has allusions to novelists and the creative process, and how a purportedly physical act can tax the mind:

As Balzac said, there goes another novel.

After having sex with her for the first time, Alvy is "a wreck," musing: "I'll never play the piano again." He compliments Annie [in a line originally credited to H. L. Mencken in 1942, and also to Humphrey Bogart]:

That was the most fun I've ever had without laughing.

Annie smokes some pot because it relaxes her. She offers him some pot, but he declines because the effects usually have embarrassing results: "I don't use any major hallucinogenics...Five years ago at a party, I tried to take my pants off over my head." Still sexually aroused, Alvy announces: "You're not going to believe this..." as he moves closer to Annie.

At a bookstore, Alvy, anally-obsessed with the subject of death and its inevitability, wants to buy two serious books for Annie to contemplate: Ernest Becker's The Denial of Death and Jacques Choron's Death and Western Thought. His hidden desire is to turn her into a likeness of himself - a death-obsessed, intellectual New York Jew. In contrast, Annie is considering buying a glossier book: The Cat Book - because she is thinking of buying a cat to cut down on her sense of social solitude. Their life experiences and interests are considerably at odds. Alvy warns Annie of his gloomy view of life, dividing life experience into two categories:

I'm obsessed with uh, with death, I think. Big - big subject with me, yeah. I have a very pessimistic view of life. You should know this about me if we're gonna go out. You know, I - I feel that life is - is divided up into the horrible and the miserable. Those are the two categories, you know. The - the horrible would be like, um, I don't know, terminal cases, you know, and blind people, crippled. I don't know how they get through life. It's amazing to me. You know, and the miserable is everyone else. That's - that's - so - so - when you go through life - you should be thankful that you're miserable because you're very lucky to be miserable.

In a Central Park scene where they sit on a bench, he cleverly makes fun of strolling passers-by who are out of earshot by giving stereotypical thumbnail sketches of them, impressing Annie with his intellectual dexterity:

• "There's Mr., in the pink, Mr. Miami Beach there. He's just come back from the Gin Rummy fund. He's placed third."
• Two lovers: "They're back from Fire Island. They're giving it a chance for a minute."
• "He's the Mafia - Linen Supply Business or Cement and Contracting."
• "There's the winner of the Truman Capote look-alike contest." [The real, fastidiously-dressed Truman Capote is cast in the imitative role - a melding of fact and fiction.

By the waterfront dock in a night scene, underneath the 59th Street bridge, Alvy woos Annie, telling her how sexually appealing she is:

You are extremely sexy, unbelievably sexy...You know what you are, you're polymorphously perverse...you're exceptional in bed because you got - you get pleasure in every part of your body when I touch it...Like the tip of your nose, and if I stroke your teeth or your kneecaps...you get excited.

Annie stutters about her love for him. And serious emotional words fail Alvy when he tries to tell Annie how much she means to him. [Both appear to have never vowed their true love for one another in their entire relationship.] He even circumvents the word 'love' and retreats into comedy to directly avoid saying that he loves her:

Love is, is too weak a word for what I feel - I lurve you, you know, I loave you, I luff you, two F's, yes I have to invent, of course I - I do, don't you think I do?

In the very next scene, Annie plans to move in with Alvy and unpacks her belongings in his place. They can live together and she can save $400/month rent on her bug-ridden apartment. Again, he resorts to comedy, disguising his own fear of commitment and loss of freedom. Ambivalent, Alvy insists that she not give up her own apartment to assure them that they're not married:

Alvy: What do you mean? You're not going to give up your own apartment, are you?
Annie: Of course.
Alvy: But but but why?
Annie: I'm moving in with you, that's why.
Alvy: Yeah, but you've got a nice apartment.
Annie: I have a tiny apartment.
Alvy: I know it's small.
Annie: That's right, and it's got bad plumbing and bugs.
Alvy: All right, granted, it has bad plumbing and bugs. But you, you say that like it's a negative thing. You know, bugs, uh - Entymology is a rapidly growing field.
Annie: You don't want me to live with you.
Alvy: I don't want you to live with me! Who's idea was it?
Annie: Mine.
Alvy: Yeah, it was yours actually, but uh, I approved it immediately.
Annie: I guess you think that I talked you into something, huh?
Alvy: No. We live together. We sleep together. We eat together. Jesus. You don't want it to be like we're married, do ya?

He even offers to pay the rent by having his accountant write the payments off as a tax deduction. Another series of issues surfaces between them. She believes he doesn't take her seriously because she is ignorant, and that's why he pressures her to take adult education college courses. Annie 'unloads' her concerns on him:

Annie: You don't think I'm smart enough to be serious about.
Alvy: Hey, don't be ridiculous.
Annie: Then why are you always pushing me to take those college courses like I was dumb or something?
Alvy: 'Cause adult education's a wonderful thing. You meet a lot of interesting professors. You know, it's stimulating.