No matter what kind of woman he's taking out nor how serious the couple, she's guaranteed to love these $100-and-under excursions — most of which will end very happily, and all of which have a gift to go with them.
For the Woman You've Only Been Dating for Two Weeks: A Hot Reservation
Why she'll like it: Cooking for her may or may not be too intimate (more on that shortly), but "going for drinks" again may lead to absolutely nothing. Middle ground: Hit OpenTable.com for a reservation at a great new restaurant — late seatings should still be available, so you'll have time to loosen up with that drink beforehand.
Don't spend more than: $100; think off-the-beaten path bistro, not the fanciest joint in town.
Goes great with: Flowers; think peonies, tulips, or gerbera daisies ($15), not roses.
What you'll get: Your first sleepover with her, hopefully.
For the Woman Who Doesn't Want to Do Anything: An Evening at Her Service
Why she'll like it: Take her literally and don't have her doanything: You make her dinner, you set the table, you fix her a drink, you do the dishes, you massage her feet, you rinse, you repeat.
Don't spend more than: $35 on a ton of good, cheap wine — boxes approved.
Goes great with: A call bell ($5). "Accidentally" throw this in your recycling bin the morning after.
What you'll get: A week's worth of relaxed companionship.
For the Clingy Girlfriend: An Hour of Ice Skating
Why she'll like it: Hand-holding, hot chocolate, sweaters — it's you that might have the tough time here. But creative (and less kid-crazy) new rinks are cropping up all around the country. Try to find one with hockey skates so you don't look like a runner-up for an ice dancing medal.
Don't spend more than: $30 on rentals and rink admission.
Goes great with: A Snuggie ($15) stands in for a cuddle as soon as you're out drinking something other than cocoa with the fellas.
What you'll get: A week's worth of contentment, and a sore ankle or two.
For the Woman Expecting You to Propose: A Spa Day
Why she'll like it: It's no ring, but it's indulgent enough for her to brag about to her friends (even with one of the great deals out there). Plus, you avoid the bait-and-switch of a romantic weekend with no payoff — for either of you.
Don't spend more than: $100. Try a facial-and-pedicure combo package. Avoid the latter for yourself.
Goes great with: Romantic dinner at home — and a big bottle of something strong ($40) for the eternal bridesmaid.
What you'll get: Another holiday off the hook.
For the Woman You Actually Want to Marry: An Intimate Video (NOT a Sex Tape!)
Why she'll like it: Sounds awful, but get her talking into your iPhone and she'll get into it. Stretch out your arm in bed and tell each other romantic things: how you met, how you make up, how you make each other laugh. Then suggest you play this video not on YouTube but at your wedding — and propose.
Don't spend more than: A few seconds on a high-quality iPhone recorder, if that.
Goes great with: You know, a ring.
What you'll get: A wife. Or a video of you getting dumped.
For the Woman Expecting Your Child: An Intimate Video-Game Session (Not Madden)
Why she'll like it: Because she ain't gonna be up for much else, and Look Who's Talking Too on the couch ain't gonna cut it. Turns out women actually like this sort of thing, so pop in a racing game or one of the throwback Mario titles into your Wii — then settle on a slightly less cheesy movie from Netflix's streaming service on the console.
Don't spend more than: $29 on that Netflix subscription.
Goes great with: The frighteningly hilarious Baby and Megame from Australia ($65 on eBay).
What you'll get: Maybe some Madden when she passes out early.
For the Lovely New Receptionist: A Lonely-Hearts Club Party
Why she'll like it: An office-laden singles night at the local dive will stave off her Bridget Jones's Diary-induced malaise and make you look kinda popular. Invite more men than women — men who know how to back off.
Don't spend more than: $40 on drinks.
Goes great with: Quarters ($2) for the jukebox.
What you'll get: Lucky, perhaps. And then awkward, certainly.
For the Ex You're Trying to Get Back: A Round or Two (Max) of Karaoke
Why she'll like it: Karaoke is so ridiculous as to be disarming, especially when Journey is involved. And crooning a song she remembers you by — not your song, a song — is just disarming enough for her to forget the breakup.
Don't spend more than: $40 on drinks. For yourself. For pitch.
Goes great with: Nothing. Premeditated gift for ex-girlfriend equals death.
What you'll get: A second chance. Maybe.
For the Woman with Expensive Taste: A (Window) Shopping Spree
Why she'll like it: Because it's shopping. Take her to your local Saks and wait, patiently, as she reenacts Pretty Womanwith a not-quite-on-sale-enough gown or two. Compliment excessively. Do not buy. Yet.
Don't spend more than: $62 for Ralph Lauren's Romance fragrance on the way out.
Goes great with: Subscriptions to BagBorrowSteal.com ($5-$10 a month for her to rent $5,000 bags) and Steal the Time ($27-$150 a week to lease $20,000 watches).
What you'll get: Repeated undressings during the try-on phase.
For the Foodie: A Supper-Club Outing
Why she'll like it: Supper clubs are like speakeasies for eating — underground and enthusiast-friendly, except they take place at the homes of local chefs, too. They even have Web sites, especially in cities like San Francisco, Washington, and New York.
Don't spend more than: $100 for dinner, although many are by donation.
Goes great with: Thomas Keller's fantastic cookbook, Ad Hoc at Home ($30).
What you'll get: A belly rub.
For the Homebody: A Cooking Class
Why she'll like it: Bonding, knives, and wine — good things all, but in that order. A good maître d' at your local restaurant can recommend a decent one-off lesson for a decent tip, which you'll recoup by dining at home the next few weekends.
Don't spend more than: $85.
Goes great with: A retro ruffled apron from Anthropologie ($32), which you might convince her to wear all by itself.
What you'll get: The end of her "secret meatloaf," at last.
For the Athlete: A 5K RaceWhy she'll like it: Even if she has to drag your limp body across the finish line, it's the tag-along-to-the-gym afternoon you've never taken her up on before. A Web search for "Valentine 5K" or "Love the Run You're With" should turn up one of many couples' runs in your nearby city. Because they're awkward, but nice.
Don't spend more than: $45 to register, which goes straight to charity.
Goes great with: A tube of Bengay ($6) and a hamstring massage.
What you'll get: She may want to work up a sweat when you get home, too. But first, a cocktail.
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