Low living in high places: scaling great heights for morally ambiguous reasons

Summer's just a few weeks away, meaning the year's flying by; time to finally admit you're never going to take up running, volunteer, or squeeze back into that red-striped swimsuit that's collecting dust under your bed. Instead, let these alternately wonderful and miserable summer months force you to fully embrace your self-destructive and -indulgent ways: Why not let your bad habits get a good tan to match yours and, while you're at it, why not do it from more enticing vantage points than the stepladder you perch next to your grimy windows? (Don't worry: Your apartment will still be just as filthy and poorly lit when you get back.) Never one to say no to a bad idea, The A.V. Club rolled off our crusty futon and hit the town to wallow in our own decadent filth; we humbly submit this guide to making this the most delightfully reprehensible summer yet.

You want to: Pay complete, licensed strangers to touch you
You should try: Disrobing and hopping on a table at Hyde Park’s Ki Massage & Bodywork (1525 E. 53rd St., Ste. 810, 773-719-7273)
The A.V. Club says: It’s a 25-year-old naprapathic clinic—meaning the practitioners on staff specialize in alternative means to treat pain and injuries—and massage therapist Kimosha Murphy insists her workspace has the best view of the lake, which obviously is soothing as well. You can get spa-like treatment here, and $80 an hour is a small price to pay to release that monkey-fist of tension in your lower back from marathon sitting sessions.
Best time to go: In the middle of the workday. Not only does the east side of the building face the lake, but it’s also near the Metra tracks—trains come by less frequently between 11 a.m. and 2 p.m., freeing you to just soak in that gorgeous view and forget about that job you should be at right now.

You want to: Pick up some tool or out-of-towner (or be the tool/out-of-towner doing the picking)
You should try: Roof, located atop the Wit Hotel (201 N. State St., 312-239-9501)
The A.V. Club says: Tuck in that shirt—and pop that collar while you're at it. Roof's posh minimalism and all-too-eager-to-bounce door staff demand patrons look their best, but its Loop location also means only the most aloof scenester, tense office worker, or uninformed visitor would ever find his way there. Capitalize on Roof's novelty while you can, soaking in the sweeping panorama of its North Loop neighbors while impressing those beautiful, sud-swilling dreamers with your tales of conquering all the hottest spots in exotic, mythical lands like River North and Lincoln Park before they realize they're paying $12 for the world's weakest Jack and Cokes.
Best time to go: After drinking three beers. Any sooner, and you won't be confident enough to blend; any later, you'll be too drunk to be cool.

You want to: Engage in adult situations while cheering for a Little League-caliber team
You should try: Grabbing seats in the extreme upper deck at a Sox game (333 W. 35th St., 312-674-1000)
The A.V. Club says: Yes there's beer, and yes there are all kinds of tasty food on hand, but everyone knows the real fun is just waiting to for you and that special someone on the third-base (get it?) side upper concourse just past section 544. Don't you kids worry about getting caught, either: With the ballpark three-quarters empty these days, you've got the place to yourself.
Best time to go: A night game in mid-June, when the weather's nearly perfect and the sunset coincides with the fourth inning. How romantic. Really.

You want to: Make a righteous yet idiotic statement about world hunger and consumerism while casually indulging in the most crass way possible
You should try: Fine dining at C-View (166 E. Superior St., 312-523-0923) with a glorious, near-360-degree view of the Gold Coast
The A.V. Club says: An offshoot of C-House on the 29th floor of the Affinia Hotel, C-View's bar menu runs the gamut of high-end gluttony, from the $15 lobster club sandwich to the $25 artisanal cheese plates. Still, if nothing says "excess" like oysters, then nothing says "disgusting excess" like ordering a dozen ($28) and throwing out 11 of them. You, dear diner, are why other countries hate America.
Best time to go: A weeknight several months from now—weekend tables have become impossible to attain since resident chef Marcus Samuelsson began competition on season two of Top Chef Masters.

You want to: Duck out of work early to save money on drinks while ogling a mostly naked lady
You should try: The elevated VIP booths at Pink Monkey (750 S. Clinton Ave., 312-663-9100)
The A.V. Club says: The view from atop the miniature throne rooms behind Pink Monkey's main stage might not be as picturesque as the lakefront or the skyline, but it does offer reassurance that you are not alone in your quest for topless strangers—comfort no restaurant or massage salon could ever even dream of providing. And while the $30 cover might sting, the club's BYOB policy will surely ease the pain—as will the partial nudity, hopefully.
Best time to go: A beautiful Friday afternoon, when Pink Monkey opens at 2 p.m. Who needs sunshine when you can make it rain?