Cheap dates: Brookline/JP/Allston

Childhood reverting (and flirting)
You can't visit Brookline without taking some time to revel in its lush greenery. Grab a pair of corned beef sandwiches at Michael's Deli and head down to Winthrop Square playground, just a few blocks from JFK's birthplace on Beals Street. Sway on the swings, flirt in the spray pool and get dirty in the sandbox—all while soaking in the outdoorsy comfort provided by the park's majestic maples. The breathtaking Minot Rose Garden includes more than 70 varieties of roses, so snag a stray stem for your beau. (We won't tell...) Winthrop Square: corner of Browne and St. Paul St, Brookline. Michael's Deli: 256 Harvard St, Brookline (617-735-3354, delitogo.com)

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Book it to Brookline
Start your evening with a talk from Brookline Booksmith's long-running author series. Bigger names like Nick Hornby and John Irving fill the Coolidge Corner Theatre, though some formidable writers also give readings at the bookstore itself. After you get your fill of bookishness, you'll need a place to reflect and converse: if it’s walking weather, skip down Beacon Street to Athan's Bakery and indulge yourself with a vanilla baklava gelato. Or for shorter distances, cross the street to Paris Creperie for a dessert crepe and a delicious smoothie. Brookline Booksmith: 279 Harvard St, Coolidge Corner, Brookline (617-566-6660, brooklinebooksmith.com). Athan's: 1621 Beacon St, Washington Square, Brookline (617-734-7028, athansbakery.com). Paris Creperie: 278 Harvard St, Coolidge Corner, Brookline (617-232-1770, pariscrepe.com)

Triple Lutz, triple espresso
Face it: skating on the Frog Pond is not an original date idea, nor a particularly glamorous one once you're amongst the insane weekend mobs. Avoid the crowds and hit the ice at Kelly Rink in JP, which offers free admission and an almost criminal $2 fee for skate rentals. Warm up afterwards with a latte at Ula Cafe, which serves a mean sweet potato sandwich. Kelly Rink: 1 Marbury Ter (617-727-7000, mass.gov/dcr/recreate/skating.htm). Ula Cafe: 284 Amory St (617-524-7890, ulacafe.com)

Have a Gas at the Pill
Get a twofer for a fiver at Great Scott on Fridays. Things kick off at 7:30pm with the quirky stand-up comedy show the Gas, followed by the indie dance night the Pill, where booze flows, hipsters cavort, and everybody dances to the throbbing bass lines of Blur and the Smiths (local bands like the New Collisions, Bearstronaut and Mystery Roar make occasional appearances, too.) If you have time in between events, dip out for a refreshing boba tea at Infusions. Great Scott: 1222 Commonwealth Ave, Allston (617-566-9014, greatscottboston.com). Infusions: 110 Brighton Ave, Allston (617-254-1122)

Pool, pizza and a pitcher
It won't win any points for classiness, but there are few better deals in town than Big City's “3 Ps” package: a cheese pizza, a pitcher of draft beer, and an hour of pool for $19.99. Provided your partner's cool with Coors and cue balls, it makes for a laidback setting to talk and show off your competitive side. The 3 Ps only apply Sunday through Tuesday, but that's probably for the best; weekends should be reserved for your more debonair dates. 138 Brighton Ave, Allston (617-782-2020, allstonsfinest.com)

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