Here’s How to Win Someone Over in One Day, the Obama Way

During much of “Southside With You” — the fictional-yet-based-on-reality depiction of the Obamas’ first date — Michelle Robinson makes clear to her co-worker Barack Obama that they are not on a date. So instead of any will-they-won’t-they drama, the central conflict of “Southside” is: How will Barack win over Michelle in one day? But it’s also: How will Michelle win over Barack in one day?

Yes, those questions go both ways. Even though their day together begins with one of them more explicitly interested in the other — you might think fictional Barack is trying too hard — they are both wooing each other. They’re getting to know each other as people, not just as co-workers, and in the process they start to fall for each other.

This is a movie, so that getting-to-know-you dance, as effortless as it can seem on screen, is highly scripted and calculating. Some of the first-date strategies in “Southside” are applicable to real life; and some, if used in the wild, would be way over the top. Not every piece of the Obama playbook works in real life. Here’s a look at their date, as portrayed in the movie, plus a Solo-ish assessment of whether to try this in your own dating life.

This post contains spoilers, but what is a true “spoiler” in this movie? We know how it ends.

Meeting up super-early. So let me get this straight: Michelle thinks Barack is picking her up to go to a community meeting. He arrives late, which she notices. But he’s actually . . . early? When Barack informs her that they have hours until the meeting starts, she feels duped. Rightly so! Picking someone up hours early for your appointed outing is manipulative and disrespectful of your date’s time. Do not try this at home! If you want to tack on a second event to whatever you agreed upon beforehand, start with the main event, and if that goes well, then suggest another activity. And always show up on time.

Making your intentions (and reservations) known. Barack thinks they’re on a date; Michelle disagrees. “I am your adviser at our law firm, and it would be tacky,” Michelle tells Barack early on. It’s a sentiment she repeats throughout the day, along with her reasoning: She has to work extra hard to be taken seriously as a woman at their corporate law firm, she says, and doubly hard because she’s a black woman. Carrying on a relationship with a co-worker would make it even harder, she reasons. And yet, fictional Barack finds a way to be persistent but not overly pushy. He makes clear that the outing can be over as soon as she wants it to be — and that it’s not a “date” till she says so.

While making your intentions known is always a good idea, this is a difficult move to pull off outside of a movie. (In real life, Barack would’ve seemed like a creep.) However, notice the way Barack made clear that, while he was calling the logistical shots throughout the day, she would call the emotional ones. (Hmm, has this guy thought about a career in politics?) Still, this is not a beginner move! If you’re having trouble reading the mood, try a simple “can I kiss you?” before leaning in for that smooch.

Show, don’t tell, that you’re cultured and worldly. Okay, it waskind of sneaky that Barack tacked an extra event on before the meeting. But! The art exhibit gives them a chance to bond and talk about something other than work. Barack and Michelle start out talking about the art on the walls and “Good Times,” but those paintings become props that allow Michelle to tell Barack a bit more about her family. Instead of exchanging information about each other in a resume kind of way, they’re leaving conversational clues for the other to pick up on: Michelle says something in French; Barack asks if she’s fluent. Michelle says a painting reminds her of Gwendolyn Brooks; Barack responds byquoting one of Brooks’s poems word for word.

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In real life, without the romantic music in the background, that poem recitation would be the mark of a showoff. But going to the art exhibit or other cultural event is something regular daters can replicate, and such outings can serve as good conversation starters.

Let the conversation wander. Conventional wisdom say that religion and politics are off-limits on a first date. Barack and Michelle notably ignore those two and add race to the mix as well. He flat-out asks her: “Do you believe in God?” She asks whether he prefers white or black women. It’s the kind of probing conversation where it helps to know the other person a bit, as these characters do. But it’s also a reminder that dates are more interesting when no subject is treated as taboo. Just take a look at this Match survey that found that talking about politics on a first date greatly increases your chance of getting to a second. Go ahead and try this at home.

Challenge each other. Throughout this date, Michelle and Barack push each other to think more deeply about the things they’re wrestling with — be it Michelle’s relationship with the law firm or Barack’s relationship with his dead father. When I asked director Richard Tanne about this dynamic, he said: “He’s into her from the start, but he falls deeper and deeper over the course of the day because she is able to point out things that other people in his life probably don’t.”

That immediate kind of intimacy is tempting to try for on a first date, but be careful. There’s a fine line between gently pushing someone to see a problem from a slightly different angle and making snap judgments about a person you’re just starting to get to know. Attempt at your own risk. This could go well or fail spectacularly.

Bring in some surrogates. Lest you forget: This is Barack Obama on this date, so there will be a rousing speech at the community meeting they finally do attend. He will be inspiring and there will be surrogates in the audience, extolling his virtues. This works in the movie — barely. Michelle knows exactly what he’s doing and calls him on it. “You’re real smooth,” she says, calling the meeting “a pretty good setting to bring a girl.”

Do not try this at home. I repeat: Do not try this on a real first date. You will come off as trying way too hard if you bring someone to a setting where everyone not only knows your name but adores you. Let your date form their own opinion of you first.


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