As a gay therapist who’s practiced in Chicago for over two decades, I’ve heard countless stories about cruising in Boystown—some exhilarating, some disastrous, and many somewhere in between. Whether you’re new to the neighborhood or a longtime Lakeview resident, cruising is woven into the fabric of Northalsted’s history, from the old days of Man’s Country to the modern hookup app era that somehow still brings us to the same bars and street corners.
Cruising isn’t just about hookups—it’s about connection, desire, and the electric thrill of possibility. But it also carries real risks, especially in a neighborhood that’s seen its share of hate crimes, robberies, and incidents that remind us we can’t take our safety for granted. Here’s what I tell clients who ask me about navigating the cruising scene safely and authentically.
1. Know the History—And Why It Still Matters
Cruising has been part of gay male culture since long before Grindr. In Chicago, places like the Belmont Rocks, Lincoln Park’s “Fruit Loop” trails, and even the third-floor balcony at Man’s Country (RIP, 1973-2017) were where men found each other when simply existing as gay could get you arrested, fired, or worse.
Boystown itself emerged from this history. By the 1970s and ’80s, Halsted Street between Belmont and Addison became a refuge where gay men could be visible. Bars like Little Jim’s, Sidetrack, and Roscoe’s created spaces where cruising moved indoors, with eye contact across a crowded bar replacing the furtive glances in parks and public restrooms.
Understanding this history matters because it reminds us that cruising has always involved risk and resilience. The gay men who came before us navigated police entrapment, violence, and a society that criminalized their desire. Today’s risks look different—but they’re still real. That historical context should inform how we move through these spaces now: with awareness, caution, and respect for the vulnerability inherent in seeking connection.
2. Trust Your Gut (Especially After Midnight)
I can’t count how many times a client has told me, “I knew something felt off, but I ignored it.” That instinct—the tightening in your chest, the voice that says this doesn’t feel right—is your nervous system trying to protect you.
Cruising often happens late at night when you’ve been drinking. Your judgment gets cloudy. That guy who seems charming at 1 AM might have been setting off alarm bells at 10 PM. If someone’s pushing you to leave quickly, getting aggressive when you set boundaries, or giving inconsistent answers about where they live or want to go, trust that feeling.
Practical tip: Before you go out, decide on your boundaries while you’re still sober. Will you only go home with someone you’ve talked to for at least 20 minutes? Will you always tell a friend where you’re going? Will you avoid leaving with strangers if you’ve had more than two drinks? Write it down if you need to. Your sober self knows what your drunk self might forget.
3. Never Walk Alone Late Night—Especially Leaving Bars Like Sidetrack
Sidetrack on Halsted is iconic—the video bar that’s been a Boystown anchor since 1982. Show tunes Mondays, packed weekends, that electric energy spilling onto the sidewalk. But here’s the reality: leaving Sidetrack (or any bar) alone after midnight, especially if you’re visibly intoxicated, makes you a target.
Over the years, there have been robberies, assaults, and even a few high-profile hate crimes targeting gay men leaving Boystown bars. In 2021, several men were attacked and robbed in separate incidents near Halsted and Belmont. The attacks often follow the same pattern: someone waits outside a bar, follows an intoxicated person down a side street or toward the red line, and strikes when they’re alone.
What to do instead:
- Leave with friends, even if you met them that night
- Use rideshare apps like Uber or Lyft—wait inside the bar until your driver arrives
- If you’re walking to the red line at Belmont or Addison, walk with a group
- Stay on well-lit main streets (Halsted, Broadway, Belmont) rather than cutting through side streets
- Consider calling the Boystown Safety Patrol at (773) 868-3200 if you need an escort to your car or the train
The neighborhood is generally safe, but opportunistic criminals know that drunk gay men leaving bars alone are easy marks. Don’t be one.
4. Screen Before You Meet—And Share Your Location
The cruising landscape has changed. Most connections start on Grindr, Scruff, or other apps before you ever make eye contact in person. That’s actually good news for safety—if you use it right.
Before meeting up with someone from an app:
- Verify they’re real: ask for a live photo or FaceTime
- Check their profile for red flags: no face pics, brand new account, overly pushy about meeting immediately
- Share your location with a trusted friend using iPhone’s “Find My” or Google Maps location sharing
- Tell someone where you’re going and who you’re meeting—send them a screenshot of the profile
- Meet in a public place first if possible, even just for 10 minutes at Berlin or Scarlet before heading elsewhere
If someone refuses to verify their identity or gets angry when you ask basic safety questions, that’s your answer. Block and move on. Legitimate people understand why gay men need to be cautious.
5. Avoid “Helping” Strangers with Problems
This is a classic setup that I’ve seen play out too many times: You’re outside Hydrate or walking down Halsted, and someone approaches asking for help. Their phone died, they need directions, they’re locked out, they lost their wallet, their friend ditched them—whatever the story, it ends with them needing to come to your place or you going somewhere with them.
This is often how robberies happen. The person seems friendly, maybe even flirty. You want to help. You don’t want to seem paranoid or rude. But here’s the truth: strangers asking for help late at night in Boystown are often not who they seem.
Better response: Offer to call someone for them, suggest they go into a bar or business for assistance, or simply say “I’m sorry, I can’t help” and keep moving. It’s not your job to save everyone, and your safety matters more than a stranger’s opinion of you.
6. Cruising the Belmont Rocks or Clark Street? Bring a Buddy
The Belmont Rocks—that iconic stretch of lakefront at Belmont Harbor—has been a cruising spot since the 1970s. It’s where generations of gay men have connected, hooked up, and found community under the Chicago skyline. But it’s also isolated, especially after dark, with limited lighting and plenty of places for someone with bad intentions to corner you.
Same goes for cruising on Clark Street near the Hollywood Beach area or parts of Lincoln Park. These spaces have history, but they also have risk.
If you’re going to cruise outdoor spots:
- Go with a friend who can watch your back
- Stay in areas with other people around
- Avoid going after midnight when the area empties out
- Keep your phone charged and in your hand
- Don’t drink heavily before going—you need your wits about you
- Let someone know where you are
The Rocks can be magical on a summer evening at sunset. At 2 AM after the bars close? That’s when things get dicey. Use good judgment.
7. Remember That Shame Is the Enemy of Safety
Here’s the thing I see most often in therapy: gay men put themselves in dangerous situations because they’re ashamed of what they want. They don’t tell friends where they’re going because they don’t want to admit they’re hooking up. They don’t set boundaries because they’re afraid of seeming “difficult” or “not fun.” They ignore red flags because they’ve internalized the message that they should be grateful for any attention.
This is what internalized homophobia does—it makes us believe we don’t deserve to be safe, that our desire is something shameful we need to hide, that we should accept whatever we can get.
Cruising isn’t shameful. Sex isn’t shameful. Wanting connection—however you define it—isn’t shameful. What you do deserve is to pursue those things safely, on your terms, with people who respect you.
In practice, this means:
- Being honest with at least one friend about your plans
- Not apologizing for having standards or boundaries
- Recognizing that being called “paranoid” or “uptight” is a manipulation tactic
- Understanding that safe, consensual encounters are hotter than risky ones where you’re scared
If you find yourself repeatedly making choices that put you at risk, that’s worth exploring in therapy. Often there’s deeper work to do around self-worth, shame, and what you believe you deserve.
Frequently Asked Questions About Cruising in Boystown
When is the safest time to cruise in Lakeview and Boystown?
The safest times are typically early evening hours (7 PM – 11 PM) when bars are busy but before the heavy drinking sets in. Weekends see more foot traffic, which means more eyes on the street and generally safer conditions than weeknights. Avoid the 2 AM – 4 AM window when bars close—that’s when most incidents occur as intoxicated people leave alone and the streets empty out. If you’re cruising outdoor spots like the Belmont Rocks, go during daylight or early evening hours in summer when other people are around.
How do seasons affect cruising safety in Chicago?
Summer (June – September) is generally safest for outdoor cruising because there are more people out, better visibility with longer daylight hours, and you’re not isolated. Market Days in August brings massive crowds to Halsted. Winter months (November – March) are riskier because fewer people are on the streets, darkness comes earlier, and icy sidewalks can make it harder to move quickly if needed. The lakefront and Belmont Rocks are practically empty in winter—avoid cruising there during cold months. Spring and fall offer moderate safety, but always check sunset times and plan accordingly.
Is it safer to cruise at bars or outdoor spots?
Bars are generally safer than outdoor cruising spots. Venues like Sidetrack, Berlin, Roscoe’s, and Hydrate have security, other patrons around, and staff who can intervene if something goes wrong. Outdoor spots like the Belmont Rocks, parts of Lincoln Park, or quiet side streets off Halsted are inherently riskier—they’re isolated, have poor lighting, and give you fewer escape routes if a situation turns dangerous. If you do cruise outdoors, never go alone and stick to well-lit, populated areas.
What should I do if I feel unsafe while cruising?
Trust your instinct immediately. If you’re at a bar, stay inside and call a rideshare or ask staff for help. If you’re on the street, walk toward populated areas like Halsted or Belmont, go into any open business (24-hour Walgreens at Belmont and Broadway is a good option), or call the Boystown Safety Patrol at (773) 868-3200. Don’t worry about seeming rude—your safety matters more than someone’s feelings. If you’re being followed, make noise, call 911, and head toward people and lights.
Are hookup apps safer than in-person cruising?
Apps like Grindr and Scruff give you more time to vet someone before meeting, which is an advantage. You can verify identity, check for red flags, and share information with friends before meeting up. However, apps aren’t foolproof—people lie, use fake photos, and can still be dangerous. The safest approach combines both: use apps to make initial contact and screen people, but still follow safety protocols like meeting in public first, sharing your location, and telling someone where you’re going.
How can I cruise responsibly while drinking?
Set firm boundaries before you start drinking: decide you won’t leave with strangers after more than two drinks, you’ll always leave with friends or take a rideshare, and you’ll check in with someone by a certain time. Consider alternating alcoholic drinks with water. If you’re at a bar and someone’s buying you drinks, watch the bartender make them—never accept a drink that’s been out of your sight. Most importantly, have a sober friend you can text if you need a reality check on whether someone seems safe.
Final Thoughts: Cruising with Intention
Boystown exists because gay men refused to hide. The bars, the street life, the cruising culture—it’s all part of our legacy of visibility and connection. But we honor that legacy by taking care of each other, not by pretending the risks don’t exist.
Cruise with confidence. Cruise with caution. Know your worth. And remember that the best nights out are the ones where you get home safely to tell the story later.
If you’re struggling with anxiety around dating, hookups, or navigating the gay social scene in Chicago, therapy can help. Our practice has been serving the LGBTQ+ community in Boystown in Chicago for over 20 years, and we get it. You don’t have to figure this out alone.
