Six Ways to Bag A Socialist Baddie
Dating advice. The Marxist way.
Everyone’s saying dating in these times is both hard and expensive, but we here at Guerrilla Press thinks that’s a capitalist way of thinking. Dating a socialist isn’t just about romance; it’s about solidarity. You can’t just think that flowers and an expensive meal will impress that snack of revolutionary; you have to bring class consciousness in your swag. But fear not, you Comrade Casanova to be, here are six date ideas on How to Bag a Socialist Baddie:
The Lakefront. Which, By The Way, Y’all Already Own.
Chicago is one of the only major cities in America where the entire lakefront is public land, and that is not an accident. That is the direct result of A-aron Montgomery Ward. A capitalist, ironically, who sued the city twice in the 1890s to keep developers off the waterfront. Tell your date this while you walk the 606 or sit on the rocks at Rainbow Beach watching the skyline. Then let it hang in the air; a rich guy once did something good for the public! Note that this, and this is true, is quite rare.
Bring a blanket. Bring a bevy. Do not bring a 12-piece from Harold’s unless you want to be chased down by pigeons.
Take The Red Line Together. The Entire Red Line.
Nothing will radicalize a person faster than riding the CTA from Howard to 95th in one sitting; not because it’s dangerous, but because it is a living, breathing reminder of a city that has been deliberately divested from, neighborhood by neighborhood, for decades. Watch how the train fills and empties. Watch how the architecture changes. Watch how the grocery stores disappear south of Roosevelt. Chicago’s disinvestment in its South and West Sides is not an accident of geography; it is a policy choice, repeated across generations. You don’t have to say any of this out loud. Just ride it together and let the city explain itself.
If they’re the right person, they’ll already know. If they’re still learning, this is not going to work.
Haymarket Square. Just... Go Stand There.
This one is perfect for May Day. It’s a small plaque near Randolph and Des Plaines. Easy to miss. Most people walk by it every day without knowing that this is ground zero for that eight-hour workday they enjoy, or increasingly hate if their boss Dan always uses the word “passionate” to mean “exploitive”. May Day, loudly celebrated by workers in nearly every country on earth except, conspicuously, the United States, comes from this corner. Take your date there. Let history do the talking. Then get an Italian beef, extra dipped.
Pour out some gravy for the blue-collar homies.
A City Council Meeting. Hear Us Out.
Chicago City Council is 50 alderpersons representing 50 wards. It is one of the most powerful municipal legislative bodies in the country, and this is also true, one of the most corrupt. A masterclass in how power concentrates when citizens don’t show up.
Meetings are public. They are free. They are occasionally chaotic in a way that is genuinely more entertaining than most things on Tubi. Take your date to one. Watch how decisions get made about TIF funds, zoning variances, and police budgets. Watch who speaks and who gets cut off.
Afterward, go and get a well-earned drink and talk about what you just witnessed. This is civic foreplay. Roar.
Volunteer Together. Pick Something Unglamorous.
Skip the one-day “Day of Service” where everyone wears matching t-shirts and takes a LinkedIn photo. That’s not solidarity. That’s performative with a tax write-off. Instead, find something that requires return visits: a weekly shift at the Greater Chicago Food Depository, canvassing with a DSA Candidate, mutual aid distribution in Englewood or Austin, where the city has decided residents need fewer resources and more thoughts and prayers.
But the gag is: there is no better vibe check for character than volunteering regularly alongside someone you’re into. You’ll learn whether they show up when it’s cold, whether they’re kind to people having the worst day of their life, whether they do the work without performing the work. That’s more information than six dinner dates will ever give you. And if they keep showing up, that’s someone who understands that love, like change, is not a feeling. It’s a practice.
Do Absolutely Nothing. On Purpose.
The most radical date you can go on in Chicago, or anywhere in the algorithmic hellscape, is one where you produce nothing, consume nothing, and post nothing. Bring a blanket to the lakefront. Watch the water. Read different books next to each other. Talk about what you actually believe: not your personal brand, not your podcast recommendations, not your five-year plan.
The lake doesn’t care about your hustle. It was here before the city and it will, at the rate we’re going, eventually reclaim several neighborhoods on the North Shore. There is something useful in sitting next to something that big and that indifferent to capitalism. It clarifies things. It can help clarify people.
And if the person next to you on that blanket gets quieter and easier and more themselves the longer you sit there, that’s not just a Baddie.
That’s socialism, bby.
Xo,
T