Okay fine, so maybe the 12 Days of Fail-Safe Girl Gifts is more like 10 Days (of 12 categories) now. Whatever. Sometimes Miss Wingman has a little too much fun on her weekends and needs to recover – apologies for the delay (but not the fun). Today’s suggestions are a mixed bag, but all make solid gift contenders.

First up we have sporty, physical activities for the girl who isn’t afraid to try something adventurous. So get out your sneakers and your belay ropes, boys, this one’s guaranteed to be a good time.

Indoor Rock Climbing: If you’re not fortunate enough to live in an area where you can do actual rock climbing outdoors (us city dwellers have to improvise), giving her a package at a place like Brooklyn Boulders is an excellent idea. This 20,000 sq ft urban playground located at 575 Degraw Street (at 3rd Ave) offers great gifting options and is open seven days a week.

Most cities have rock climbing facilities that include equipment rentals and a few lessons to boot, and Brooklyn Boulders is no different. Packages like Learn The Ropes cost $75 for two day passes, one equipment rental and a belay class for beginners. There is also a Learn To Boulder class ($45), or you can set her up with a membership for $120/month.

If you’re so inclined to take on the altitude as well, join her when she goes – activities like this are great at fostering trust and communication building among couples.

Or, if climbing isn’t her style, you could always opt for some high-flying alternatives. Trapeze School New York offers classes in flying and static trapeze stunts, silks, balancing/acrobatics and even trampoline instruction. Is there anything better than that?

Chelsea Piers also offers a variety of sports-related activities you could purchase in advance, like golf packages, adult Parkour instruction (really, they do), batting cage rental or even sailing school. Check their website for gift package ideas – and check out the endless options for fun.

Perfect for: Any woman who likes to move (and kick a little ass). Dating timeline appropriateness: Any. You can do something small cost-wise or something loftier, but all of these just say “fun” – so don’t worry about commitment issues or strings attached. What it says about you: That you, in a word, rock (pun intended).

If she prefers a more sedentary lifestyle, you can always opt for a gift that keeps on giving all year long, like a subscription to her favorite magazine or a membership to a wine of the month club. Magazine subscriptions may seem impersonal, but really they’re a guilty pleasure that we wouldn’t buy for ourselves if we’re being cost-conscious these days. Plus, whether she’s into US Weekly or The Economist, every girl loves getting something in her mailbox that isn’t a bill from time to time.

Wine clubs are another solid way to give her a special treat (plus she’ll probably be uncorking those bottles and sharing them with you anyway, score!). Since sites vary in shipping costs, best values and best selection, check out services like Wine Club Guide and Wine Club Reviews to read up and compare before choosing which service is the best fit.

Perfect for: Any woman who likes to curl up with a good bottle and a blanket, or just the girl who likes to flip through the glossies in her free time (read: indoors girls). Dating timeline appropriateness: Any, unless you think that the subscription might outlast your relationship! What it says about you: I wanted to find a way to make you feel special all year long.

Finally, whether you can afford a vacation or just a stay-cation, altering her scenery is always a welcome change. Providing travel is expensive unless you utilize airline miles, car rental or hotel points (and even then, it’s still not free). If you can’t whisk her away to a tropical landscape, how about trying some place closer to home?

Lafayette House in NYC’s East Village is positively delightful. It’s cozy but still hip, and quaint enough to make you forget you’re still in the Big Apple. Room rates vary depending on booking dates and amenities but generally run $200 – $400 per night. Check out their thoroughly charming website for photos and booking information.

Perfect for: Any female. Literally – any female. Dating timeline appropriateness: Flexible. So long as you’ve spent the night together somewhere else (or even if you haven’t), it’s a fun little escape from the ordinary. Plus, you get fresh towels and swankier digs. What it says about you: I like you enough to want to keep you all to myself for a night or two.ETIQUETTE WINGMAN

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Have you ever met a girl who doesn’t like jewelry? Me neither. But, for some reason men are usually confounded by where to begin when jewelry shopping (it’s not like it’s for that type of ring, jeez). No worries – that’s where I come in. Here’s a list of baubles I’ve come across that any woman would be happy to unwrap. And, because cost can be a factor, these sparkly pieces run the gamut price-wise. Hey, no one said you have to drop Elizabeth Taylor gems to get her to smile.

My favorite jewelry hands down is by designer Ted Muehling. Though hardly a well-kept secret, Muehling’s tiny treasure trove of a store is tucked away in NYC’s Tribeca neighborhood (newly located at 52 White Street – blink and you’ll miss it). Known for carrying much more than just jewelry – his candlesticks are beyond – Muehling has cultivated a simple yet elegant jewelry collection. His earrings vary in price, but start around $200 (going way up from there), and are perfect for every day wear or special occasions.

Anchors aren’t just for sailors and hipsters anymore. Me&Ro features this maritime-themed Hope ring for $150. Available in sterling silver on their website, this dainty little piece is just divine.

For the optimistic female, this smiley face necklace by St. Kilda is sure to make her, well…smile. Available online or at the mecca of all female I’ll-take-one-of-everything spaces in NYC, ABC Carpet & Home, this delicate pendant retails for $198, and these celestial star stud earrings will cost you a pretty penny more at $264 (but they’re so cuuuuuute). I know, I know, to New Yorkers somehow that sounds reasonable.

If silver’s not her thing, designer Daphne Olive’s nature-inspired pieces are just adorable. This mini pine cone necklace and also this spiky onion pendant are playful and quirky. Contact the designer for pricing, but boutiques like Table Top in Washington D.C.’s swanky Dupont Circle neighborhood carry a large collection of her pieces.

For some slightly more mainstream finds, designer Lulu Frost has been contributing some amazing vintage-inspired pieces to J.Crew stores around the country lately. These earrings retail for a more modest $65, or you can opt for one of Frost’s bangles, like this lovely $45 art deco bracelet. Reminiscent of something she’d rescue from her grandmother’s jewelry box, Lulu (and J. Crew) almost never miss.

For the girl who loves a good chunky cocktail ring, designer Alexis Bittar (despite the name, Alexis is a dude) sure has a knack for giving good hand. This crystal-encrusted sparkler is a fun addition for a night on the town ($225), or else Bittar’s lucite pieces are a favorite of mine, like the ring featured here (available in many colors). He occupies some space in Soho/the West Village/the Upper East Side, but his jewelry is also available at several retailers as well as online.

For the girl who is decidedly less girly, another one of my all-time favorites is anything by Giles & Brother (above bracelet $125) . Their edgy collections are the companion offshoot to the equally badass (yet WAY less affordable) Philip Crangi line. I would pretty much commit murder for several of Crangi’s pieces, but Giles seems to capture the same industrial aesthetic without breaking the bank. By using things like rail road spikes, fish hooks and tiny nails as inspiration, G&B is a solid choice for the girl who isn’t afraid to wear it. *Note, considering my site design, Miss Wingman should probably find these under the tree this year.

And finally, a fun twist on a traditional retailer is brought to you by the collaboration between Frank Gehry (yes, that Frank Gehry) and timeless jeweler Tiffany & Co. Though many of this architectural giant’s pieces are uber-pricey (even more than the above $525 option), I’ve long been a fan of rose gold, so perhaps your lady is, too. Just be careful, when pulling out one of Tiffany’s signature light blue boxes (in ring size, no less) her heart may start racing. You might want to clarify your intentions, first.

All of these choices pretty much say the same thing, “I get it, you like jewelry.” But also, “I carefully considered your taste when choosing this,” (an obvious lie, since this site tipped you off; it’s our little secret, promise).

The dating timeline appropriateness for these is obviously for anyone who has been together long enough to give the gift of jewelry, which is a pretty clear sign that you’re into her. Take into consideration that most of these aren’t cheap, and that also plays into how serious your feelings (and retail intentions) are – or what your budget is, which is an understandable limitation.

Whatever you choose, just remember that jewelry is personal and subjective, so don’t be offended if your choices miss the mark. I’ve always believed that if a man is going to spend the money, you might as well make sure she’s going to like/wear it, even if that requires allowing her to exchange it for something that’s more her style.

That said, I don’t know that I’ve ever actually swapped out anything a boyfriend has bought me, since I didn’t want to diminish the effort he put into carefully choosing the gift, but I can certainly understand the inclination.

Pay attention to what she wears every day, what hints she drops about pieces she’d like (girls do that), but most importantly, just go with your gut. And make sure it’s the girl who shines more than anything.ETIQUETTE WINGMAN

Have any great gift ideas for Miss Wingman? Share the wealth. Email me at and maybe your idea will be featured in an upcoming 12 Days of Fail-Safe Girl Gifts alongside other standout lists and suggestions. Either way, keep it right here for much more gift giving wisdom.

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After yesterday’s list of holiday gifts highlighted things that can’t fit in a box, it’s only natural that today’s list features things that only fit in an envelope. That’s right – put some tickets in her stocking this year. Whether for live music or sporting events, you can’t go wrong taking her to see something she loves in person.

While I lean heavily towards the “there’s nothing like a concert” direction – or maybe I’m just still disgusted by the NBA post-lockout – here are some of the more coveted (Big Apple) shows she might want to add to her stub collection (sorry other cities!):

  • Phish at Madison Square Garden (12/28, 12/29 and a 12/31 NYE show as well - if you can get tickets)
  • Also solid New Years Eve shows: Matt & Kim (Hammerstein Ballroom), New Kids On The Block (if she has a sense of humor like that – and you have nerves of steel – at Roseland), Fitz & The Tantrums (Blender Theater at Gramercy), Gogol Bordello (Terminal 5).

And if she can wait a little longer, some 2012 dates that could make for great gift options are:

  • Chris Cornell (1/7 Times Center)
  • Preservation Hall Jazz Band (1/7 Carnegie Hall)
  • Peter Frampton (2/18 The Beacon)
  • Flogging Molly (2/23 Roseland)
  • And the mother of all coveted tickets, the 3/22 encore date of The Black Keys’ already-sold out March show (3/12) at Madison Square Garden. But you better wake up early for these, tickets go on sale Friday 12/16 at 9am.

Of course, there are other 2012 tours in the works, like Coldplay and Red Hot Chili Peppers, not to mention several more rumored shows (please please pretty please Beastie Boys), just in case this list doesn’t suit her concert palette.

And, since Santa wanted you to have other ticket options, if you can’t catch the end of the NFL season, you could always take her to an NBA game (insert eye roll – I’m sticking to college hoops this year) or hit up my favorite sport to watch live – hockey. New York Rangers fans don’t have to wait long to gift her, they play the Islanders on 12/26 – always a fun rivalry.

If you don’t live in the greater NYC area, you can always check what’s playing in your neck of the woods on sites like Citysearch, or just stalk the tour dates list on her favorite band’s website (or sign up for alerts, too).

So, whether you want her to rock – or be a jock – this holiday season, you can’t go wrong with the gift of paper…tickets. Ho Ho Hope she likes them! (OK, cheesy puns over, won’t happen again). And, make sure you keep it right here for much more of Miss Wingman’s 12 Days of Fail Safe Girl Gifts.ETIQUETTE WINGMAN

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Yesterday I gave you a rundown of personalized gifts for your favorite female. Today, I’m encouraging you to go big – as in, things that won’t fit in a box. That’s right – instead of giving her a “thing,” how about getting her an experience instead? Making memories is what it’s all about, so here are some fun ways to spend her time (and yours, too).

Up in the air - If she’s always looking for ways to see things from a new perspective, how about from above? Hot air balloon rides offer an aerial view of awesomeness, especially if you take her at sunrise. For city dwellers, seek out the nearest scenic area – they likely have balloon tours. In the NY/NJ/CT area alone there are options like Above The Clouds Inc., or for a view of what upstate NY has to offer, try Adirondack Balloon Flights‘ tours of the Lake George, Adirondack and Saratoga Springs areas (full disclosure: I grew up there, the views are unparalleled, hence the bias).

However, there are three things to keep in mind if you go this route -  the first is cost. Tours start at around $169 per person for 30 minutes in a non-private basket and can go up to nearly $1000 per couple depending on duration, private rides and champagne/food inclusion.

Secondly, these rides are wind and weather permitting, so if you don’t want to wait on Mother Nature, you can always try a helicopter tour instead. Manhattan has some great options, plus she can see what the city has to offer without the shuffle of the crowds. Sites like All New York Tours offer a solid rundown of your aerial options.

Finally, take into consideration her comfort level. Once upon a time I was surprised with a particularly thoughtful hot air balloon ride, but since I am deathly afraid of heights (see? I can throw myself under the bus, too) we decided to forego the experience. Though the gesture is what really mattered (and it does score major points for romance), if the thought of soaring in an open basket terrifies her, obviously opt out.

Perfect for: Any girl, so long as she doesn’t share my fear of heights! Dating timeline appropriateness: Any – except unless you’re a baller, I can’t see dropping this much cash on someone you’re newly dating. What it says about you: I like adventure and I want to share something awe-inspiring with you (swoon).

For a more grounded experience, how about letting her learn something she’s always talked about, like a language?

Gifting her with French classes is the perfect way to say Je t’aime to your cherie this year. Also, choosing something that she wants but wouldn’t normally spring for cost-wise is always a treat.

The French Institute (Alliance Francaise) offers 11-week and 5-week intensive courses for beginners, but can cost between $315 and $585 for sessions depending on frequency. (Hey, I never said knowledge is cheap). Obviously this requires some juggling with her schedule, so if you prefer the luxury of leisure time and choosing any language, there’s always the Rosetta Stone route as well.

Perfect for: Any girl with a desire to learn and the discipline to see it through. Dating timeline appropriateness: Same as above – any, but since it’s costly let your wallet dictate how much you really like her (kidding). What it says about you: I really pay attention and respect your desire to better yourself. This proves to her that you were listening.

And finally, if you’re looking for an experience of a different kind, how about something a little unconventional, like a glass blowing class? I know, it sounds a little odd, but stay with me… The art of glass blowing is something you just have to see to appreciate, plus you come away with cool keepsakes and bragging rights that you made your wares yourself.

NYC offers some well-respected options, for instance Scanlan Glass in Brooklyn’s funky Red Hook neighborhood. Classes can be private or semi-private and are offered on weekends, but as with everything, come with a steeper price tag for privacy ($300 for a 2-hour session for 2 people, so join in!). They offer beginner and 2nd level classes, as well as boasting an impressive gallery. Check their website if this sounds like something she’d enjoy.

Perfect for: Artsy girls, or girls who just think it’s badass to play with molten fire. Dating timeline appropriateness: Any, it’s a cool experience no matter what your commitment. What it says about you: I’m creative and unique – two refreshing qualities in a man.

That’s it for Day 2 of Miss Wingman’s 12 Days of Fail-Safe Girl Gifts, but check back for more holiday options. Have an idea you’d like me to highlight? Ever received a standout gift? Share it and maybe it’ll be featured – email suggestions to, and keep it right here for more gift-giving wisdom.ETIQUETTE WINGMAN

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‘Tis the season for crackling fireplaces, cozy sweaters and holiday cheer…annnnnnd guys scratching their heads in utter gift-giving confusion. Fear not, men, I’m here to help. With all of the cheesy Holiday Gift Guides being offered, I think it’s better to hear the brutal truth, for girls from a girl. Consider me Santa’s little smartass elf this year (the best kind, in my opinion).

Starting tomorrow, I will be bringing you Miss Wingman’s 12 Days of Fail Safe Girl Gifts, a comprehensive guide of suggestions and advice. That way, if she hates your present, you can blame me. A lot of pressure? Maybe, but I’m up for the challenge.

But, before I kick off my list, I wanted to offer you some guidelines that hopefully will serve you well in your pursuit of the perfect present. As long as you keep these points in mind, she’s sure to unwrap something stellar this year.

  • Know Your Audience: The single most important ingredient in a successful gift is playing into her likes and dislikes. Guys always get hung up on the cost or the originality, neither are terribly crucial. It’s not about the thing, it’s about the person – always remember that.
  • You Can’t Go Wrong With A Memory: Since we seem to be OD’ing on “stuff” nowadays, try giving her something she really wants – your time. Find something fun for both of you to do together and book it. Just remember to keep the above rule in mind when choosing said activity (despite your best intentions, a technology-free cabin getaway for a Blackberry addicted workaholic may cause her to short circuit, get the idea?).
  • Never Buy Us Clothes: Unless there is an item that you are DEAD CERTAIN she wants, you’ve seen her try it on and know her size, never ever ever buy a woman clothing, it’s too personal. We’re picky, we body obsess, it’s a disaster. Just avoid it, trust me.
  • It’s About Our Taste, Not Yours: Does she like heart-shaped things? No? Then you’d do well to avoid them, boys. While you tend to think we like anything sparkly and girly, some of us pass on pinks, hate hearts and don’t even get me started on glitter and fur. *Note, this extends to gifts that are more for you than us. I’ve said it a million times and I’ll say it again: lingerie and Lakers tickets are only altruistic if you’re dating Carmen Electra or Marv Albert.
  • Cost Is Not Nearly As Important As You Think: Unless your woman has shown you she cares about price tags – and believe me, if this is her you’ll know – don’t get hung up on how it looks in our eyes. Some of my most favorite gifts ever have been modestly priced. The key is thoughtful, thoughtful, thoughtful. 
  • Use Your Resources: Does she have a best friend she tells everything to? A sister she goes shopping with? Anyone in her inner circle who would know? Use this person as a sounding board. Two minds are always better than one.
  • Grand Gestures Are Appreciated But Unnecessary: If you tend to be an over-the-top kind of guy, that’s your decision. But that doesn’t mean what she finds under the tree (or menorah, we’re equal opportunity advice-givers here) has to be an all expenses paid cruise or a constellation named in her honor. The pressure to do such things usually comes from within, playing it safe is just fine by us.
  • Give Back: You cannot go wrong with a gift that involves some sort of charitable donation, helping people in her name, a memorial to one of her loved ones, or even a scholarship or endowment. If she blisters when she learns that there’s nothing “tangible” to unwrap, you might have a grinch on your hands.
  • Avoid Living Gifts Unless You Know She’s Up For The Responsibility: If she’s dying for a pet (and her plants have a good survival rate) then you’re probably safe. But if she can’t even remember to pay her rent on time, have mercy on the poor creature who has to call her mommy.
  • Don’t Be Afraid To Do It Yourself: Making her dinner, writing her a song or building/planting something with your own two hands is a meaningful way to say you care. Of course, it might also say that you’re cheap (kidding!) but mostly, it says that you put some time into making sure she likes it – which is appreciated year ’round.
  • Give It To Her Privately Unless You’re Confident She’ll Love It: Nothing says “Ho Ho How could you?!” like putting her on the spot. Yikes.
  • You Can’t Go Wrong With Personalization: Monogramming isn’t just for The Donald anymore, and these days you can even customize your candy. Finding a way to incorporate an anniversary, her initials or even just engraving a phrase is the kind of thing we go crazy over.

That’s it for now. I’ll get more specific beginning tomorrow, but for now think about all of this when you’re hitting the stores – actual or online. I’ll also be breaking it down into what type of woman each gift is great for, what it says about you, and how long you should be dating before you give her each present, just to avoid the awkward sound of crickets. Rest easy guys, I’ve got you covered.ETIQUETTE WINGMAN

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