Is it me or does every man, once he gets to 30, only date women 5-7 years younger? If I had a dollar for every guy friend who’s now dating a 24-year-old, I’d have a serious financial windfall on my hands. This isn’t a new trend, but it is one that makes us women raise an eyebrow – and form an opinion or ten. Maybe it’s because it’s March and Miss Wingman has a birthday approaching, but getting older has been on my mind lately. And now, lucky you, it’s on my keyboard too.

If age is a case of mind over matter, then it shouldn’t matter in regards to relationships, right? Wrong. Women mind, and what we think matters – if you ever want to end up with one of us, at least.

This isn’t the stereotypical bitter-older-woman-hating-on-younger-girls story, on the contrary I completely understand the draw. But it is an appeal to think about what your actions say to the female population. And ladies, don’t think you’re off the hook either. I’ve got some choice words for those of you who only date older men, too, so sit tight.

Guys who date women that are fresh out of college might as well be wearing a billboard that says, “I’m not looking for anything serious.” It tells us that you’re only interested in looks or a casual set up, because a woman that age likely won’t be checking her watch and tapping her foot any time soon waiting for a ring or a commitment. Not in the Northeast or California, at least. A guy who serially dates young women and then tries to date someone his own age will automatically garner some skepticism, as if we’re not sure you could really be serious about us if you’ve never stepped up to the plate until now. We want you to be, but we’re just not sure we’d like to be your trial run.

That’s not to say that women 25 and under aren’t mature, intelligent and sophisticated in their thinking, on the contrary I think they have those things in spades. It just means that they’re just getting started having fun, and they won’t be looking to settle down any time soon. If you’re not “done yet,” you don’t care if the person you’re dating isn’t done yet, either. Having no pressure is the biggest draw, but if you’re dating her when she heads into that Quarter Life Crisis freak out stage that most of us hit, you could be a casualty of her youthful wanderings, so be warned.

Women are equal offenders, having long fallen into the pattern of dating older men. Maybe that’s why guys opt for the younger model, partially as payback for their high school and college years when women treated freshman males like plankton – the lowest form of life in the romantic food chain.  So then it’s no wonder that, as soon as we hit our late 20s and 30s, we end up dating men who are closer to 40 – they’re the only ones who seem to have their acts together.

Hold it right there – I said “seem to” have their acts together, not that they’re the only ones who do. In my observations, guys want to be established and have (at least somewhat) arrived at the man they’re trying to be before feeling like they can settle down with someone. So, the later we catch them in life, the more chance there is that they won’t flake out on us like their younger counterparts. Plus, they’re not afraid to show women that they appreciate us – arguably the biggest draw of all. This might sound like a money thing, but in reality it’s a maturity thing. Money is easy to come by, but maturity? Not so much.

The flip side to all of this is that women fundamentally want to end up with someone who feels like their peer. I’m fine with dating a few years older, but after a certain point it just starts to feel wrong – like a creepy old man. Maybe it’s because I’ve never stopped thinking of myself as 20-years-old, but if the man I’m dating can’t accompany me to a fratty bar and dance with my friends and I to cheesy music every now and again – as we’ve been known to do – we might be doomed in the dating department. There’s a difference between being a grown up and taking yourself too seriously, and it’s a fine, fine line.

As for women dating younger men, I support it but my question to the guys is: Really? What’s in it for you? Either you have a true appreciation for a woman who knows what she’s all about, who she should surround herself with (and who not to), what she wants and where she’s headed…or else you just want to be able to tell your friends you took down a Cougar. I’ve dated much younger guys, and while it’s fun, it fundamentally makes you wonder if you’re just going to end up an anecdote. Like the time you dated a red head. Or an identical twin. (I’m kidding, some of my most favorite people are red heads – and now they hate me).

So where does this leave us, then? Hopefully at a truce. Women – at least this woman – would like to date men in our own age group. And, if more men would shrug off the Peter Pan syndrome, we’d be happy to forego the older guys. But only if you boys promise to stop thinking that every single woman over 25 is trying to pin you down into marital submission. Some of us aren’t in any hurry to be wifed up. Some of us are content to just sit tight. Some of us have faith that it’ll all shake out in the end… and if you need us, we’ll be over here enjoying life in the meantime.

If you care about the person you’re with, trust them, and can agree that neither one of you is going anywhere anytime soon, then that should be enough. Granted, not every female thinks like this, but more of us do than guys tend to realize – so give us some credit, please.

I know it’s tempting to go for the woman with the 24-year-old ass (you’d be crazy not to, frankly), but equally important is the woman who has had the time to cultivate a strong sense of accomplishment and self. But these things only come with time, it’s as simple as that. You should aim to find a female who wants to be with you, but doesn’t need to – there’s nothing sexy about being dependent.

Likewise, be patient, ladies. If the man you’re dating hasn’t arrived at the life he wants to lead yet, rather than pointing it out, be excited to see what he will do with his potential. Encouraging a guy to be the best version of himself and realize his goals is preferable to pointing out his shortcomings all the time. If you tell him you think he’s going to end up disappointing you, you’ve just solidified that he will. It’s a self-fulfilling prophecy, not to mention unfair.

So the moral of the story is this: age matters, but maturity and mindset matter more. Life experience, perspective and a generally solid set of values is key – and they can come in all different ages, shapes and sizes. Just try not to be a total cliche, and we’ll do the same. Maybe one day we can all meet somewhere in the middle…but I won’t hold my breath. Unless it’s to blow out my birthday candles.THAT’S WHAT SHE SAID

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Whilst trolling the Interweb for compelling things to share, Miss Wingman stumbled across a fascinating read in the NY Times. The article talks about the quirky habits we develop when living alone, and it got me to thinking about how difficult it is for us to let people into our weird little worlds – which is essentially what we do in relationships. It’s OK to be an odd duck when we’re behind the privacy of closed doors, but when those shutters get thrown open for the world (or the person you’re sleeping with) to see, that’s when things get interesting.

According to this assessment, as someone who has lived alone for years, I’m not alone in my strange apartment-dwelling ways. I, too, stand partially clothed in my kitchen preparing a snack. And closing the bathroom door? What’s the point if there’s no company over to shield oneself from?! I fully support it. I sometimes say things out loud to no one in particular, and I’ve come to accept the fact that the nice people in the conference room across the way have probably seen me naked on more than one occasion. So be it.

But, this does mean that one day I’ll have to adjust my bra-hanging-from-the-coat-rack ways to accommodate the (hypothetical) man in my life, unless he has a particularly good sense of humor when it comes to laundry.

And sleeping hours? Don’t even get me started. Anyone who could peer into my apartment at will would likely witness me wide awake, typing away or catching up on my DVR at 2am. My neighbors now think nothing of seeing me heading to the gym at 10pm or sauteing up some dinner at 11:30. I’m certain I keep vampire hours. We’re a strange breed, us solo dwellers, and one day we’ll be forced to change our spots (or at least show them to someone else).

The same goes for men, however, in adjusting their living and cleaning habits to eventually domesticate themselves enough to share a space with (read: not horrify) someone of the female persuasion. Suddenly you’ll not only have to close the bathroom door, but you’ll be asked to put the seat down, take your hand out of your shorts when couch lounging, and probably even stop screaming like a maniac during playoff games. Oh the travesty…So enjoy it while you can, boys, freedom is a fleeting thing.

Eat peanut butter right out of the jar, let your laundry pile up in the corner and blare your music first thing in the morning – or maybe that one’s just me. Revel in your solo living as long as possible, because one day we might actually look back on our tiny apartment days fondly and wish we’d appreciated them more. I’ll probably still sleep sideways in my bed, though, so I hope I end up with a man who doesn’t mind occupying a small portion of my mattress real estate.

But, we are capable of cleaning up our acts, we just need to be really, really sure before taking the plunge to live with someone. It’s a huge decision and one that, in this girl’s opinion, should only be arrived at when you’re certain that your names will one day occupy a marriage license, not just the same mailbox. The quickest way to get to the bottom of your compatibility is by living with your significant other. And if after a few months of wiping toothpaste out of the sink and enduring their Sounds of the Ocean Sleep CD you don’t want to murder each other, you’re probably fine. We just have to step outside our own comfort zone (which widens the longer we live alone) and consider another person’s habits. Because sometimes the easy part is sharing a life, the hard part is sharing a living space.GEEK WINGMAN

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Neil Sedaka said it best, breaking up is hard to do.

No one enjoys the moment when you realize that your relationship has run its course, and that the person you’d thought would be in your life for the long haul (or the short run, depending on your intentions) will henceforth be referred to as “the Ex.” Even worse than that is coming to terms with the idea that her – or his – role in your life is now over, as you watch their image get smaller and smaller in the rear view mirror.

But the undisputed worst part of parting ways is the ceremonial Dividing of the Stuff that inevitably occurs, be it retrieving discarded items or in the larger sense (read: friends and hang out spots). “Happy trails to you, now give me back my stuff,” would most aptly describe it. And, if the person you’d been dating is even remotely reasonable, she or he should cede the spoils of love back to their rightful owner.

Unfortunately, it doesn’t always go down like that.

That’s why there needs to be a set of rules to steer this awkward – and often bitter – two step. Even if they’re informal, they should be understood. So, Miss Wingman is here to offer you the gentlemanly guide to custody arrangements. Pretty please pay attention.

Actual stuff: This one’s easy – whomever it belonged to, it gets returned to its rightful owner. If it was hers, she gets to keep it, yours and it goes back to you. The only exception is in matters of gifts: Barring any big ticket items or major declarations of love (read: engagement rings) this rule almost always applies. But, if you were gifted something lavish and your gut tells you it’s not right to keep it, be like Spike Lee and Do the Right Thing. Give it back.

“People” stuff: If your friends are loyal they will perform the ritual parting of the sea and go back to whomever they were originally friends with post-Relationship Nuclear Winter. This is the best argument I can use to emphasize why you should never rely on someone you’re dating for your entire social life, 1) Because it makes you pathetic and 2) Because you’re going to lose all of your friends if/when you call it quits. Also, if you were friends with someone who ultimately sticks by your ex in the end, it’s either because you did something he or she can’t get behind, or because they secretly liked her better all along. Either way, it’s a prime opportunity for some introspection, so use it.

“Place” stuff: This gets divided into two parts. If it was your go-to place prior to your relationship, it should go back to being your haven once she’s out of the picture. This applies to restaurants/bars, parks – hell, even places of worship. Does that last one sound ridiculous? Of course since my life is fodder for all sorts of crazy stories, this one applies to me.

Someone I briefly tangled with (though not classified as a boyfriend) now goes to my church after I mentioned to him that it was chock full of young, good looking people in a hip neighborhood. He began going there after we stopped hanging out – presumably to pick up women, since he lives nowhere near it – and avoids saying hello or making eye contact though we’re mere pews apart every Sunday. Then he scurries out quickly at the end to avoid confrontation (of the benign, social kind at least). And yes, I still go to church, whatever.

I glean two things from this example: First of all, that it confirms my suspicion that the guy wasn’t worth keeping around anyway. Secondly, that he’s lucky the saying, “What Would Jesus Do?” applies, or else I’d be a lot less holy in this criticism. Who steals a church, anyway?

Am I unapologetically calling him out on this forum? Yes, yes I am – for educational purposes of course (wink). Heed this advice, boys – if you’re going to disobey the rules of ownership, at least man up and acknowledge it, especially if you have a face to face run in with your former flame. It helps keep things civil, and it doesn’t make you look classless. I chuckle every time I see him, I just can’t help it.

The flip side to the “places” coin is that, if it was a place that the two of you discovered or frequented together, you wont want to be there anymore anyway, right? Why revisit a painful reminder of what once was? As much as it sucks to abandon these relationship landmarks, it’s probably best. And I would advise against bringing new dates to these places once you move on, too. Start fresh, it’s only fair.

Of course, things are much more complicated when you either lived with your ex or were (yikes) actually married. For the latter, let the law deal with it – I can’t even begin to go there – and for the former, lean heavily on this rule of thumb: Whoever has to suffer the inconvenience of moving out should be afforded as many, “Here, you can have this…” moments as possible – so long as it was an amicable split.

But if the party moving out cheated, lied or committed some other really egregious error, then just consider yourself lucky if your ex didn’t change the locks and keep your stuff, or toss everything you own onto the front lawn. You know what they say about hell having no fury…

The way someone conducts him or herself in a break up is very telling. If you know the person you dated really loved something and it was inconsequential to you, leave it for their enjoyment. Also, try to remember that if you cared about someone once, you should be considerate of their feelings always.

But the reverse is also true. If they really cared about you and know that they’ve caused you immense suffering and can still live with themselves, this is equally telling. It takes a specific type of person to be able to sleep at night, and it’s not the type of person you want in the end.

Whatever the circumstances of the demise, realize that these parting acts will leave a final impression of you to the person you once valued, and maybe still do. There’s no steadfast way to get over a break up other than excessive amounts of time and/or perspective, neither of which are easy to swallow.

But eventually, for your own sanity, you’ll have to let go of that picture of the life the two of you shared that you’ve been white-knuckle clasping and put it away. In a box. And then tie the box off neatly with a bow. And set it down.

Just as long as it’s on your side of the room.ETIQUETTE WINGMAN

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Maybe it’s because I’ve been traveling a bit lately (and still not done), or maybe I just feel the need to unload some tracks on all of you. Either way, the dramatic swing between time spent behaving badly and the quiet lull of airport downtime has caused an interesting playlist to emerge. So, in honor of the long weekend, here’s a list of solid songs I’ve had in heavy rotation, for your President’s Day enjoyment. If you listen closely enough you can almost chart the course of my weekend’s antics.


And just to ensure you that this is Wingman relevant, you can play this on long drives with your girl sitting shotgun. She will most likely approve…at least I think so.

“Keep You Right” – Blind Pilot

“Cough Syrup” – Young the Giant

“Into The Fire” – Thirteen Senses

“If You Run” – Boxer Rebellion

“No Surprises” – Radiohead

“Love Interruption” – Jack White

“Bright Lights” – Gary Clark, Jr.

“The OtherSide” – The Roots

“Little Black Submarines” – The Black Keys

“Bad Girls” – M.I.A.

“Can’t Let Go” – Lucinda Williams

“Tighten Up” – The Black Keys

“Under Cover of Darkness” – The Strokes

“We Are Young” – Fun. feat. Janelle Monae

“For You and Your Denial (acoustic version)” – Yellowcard

“Whatever (Folk Song in C)” – Elliott Smith

“The Colored Night” – Blind Pilot

“Check the Rhime” – A Tribe Called Quest

“Hey Jude” – The Beatles

“New York” – Blind Pilot

“Bring It On Home To Me” – Sam Cooke

And there you have it: my entirely schizophrenic playlist as of late. Do with it what you will, but it has served me well thus far. I hope it does the same for you.iWINGMAN


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After spending some time on the other coast, I’ve realized that the dating scene – at least on surface level – looks different depending on what city you call home. New York and LA might as well exist on different planets.

But, there are two fundamental truths that ring true in both places: people (for the most part) just want to find someone to call their own, and that person will almost certainly not be found at a bar. This idea is hammered home this week by Matt from LA’s tale of dating gone wrong. I hope you enjoy it.

The Swap: “I don’t know if this story can technically be considered an ‘online dating’ horror story exactly, but since it started out that way I think it fits. I met this girl online and after emailing/talking on the phone for a week we decided to meet. She’d seemed cool right up until that point, but then when we finally had a conversation face to face it was just…crickets. She was cute but not terribly high energy and we were struggling to think of things to say. So, we parted ways early and my friends met me out to salvage the rest of the night.

Turns out I met another girl at the same bar later that night who seemed pretty cool (OK hot) and she was with some friends, but she promptly ditched them and we started taking shots. Second girl seemed normal enough, she told me she was in grad school, was 23 and had moved out here a year ago. We started talking about how bad my first date had gone and she and I hit it off comparing bad online dating experiences with each other. I guess we both got pretty drunk (at one point she disappeared for a half hour), but by the end of the night she and I left together and went back to my place.

We hooked up for a while back at my apartment and then she excused herself to use the bathroom. When she didn’t return right away I went to check on her and found her nodding off on the toilet (not hot, by the way). Even though she was embarrassed she came back into my room. Nothing kills the mood like seeing a girl with her pants around her ankles, things were pretty much done after that.

I must’ve passed out not long after, because when I woke up in the morning she was already gone. I guess at some point she must’ve migrated out of my bed to the family room, but I slept through it. I didn’t realize it until I headed to the kitchen and saw a huge wet stain on the cushions where the girl had obviously peed on my couch. Yup. What girl does that?! I also found out later that one of my friends made out with her at the bar accidentally before he realized that she’d been talking to me. She was coming out of the ladies room when it happened. Pretty sure that qualifies as a horror story in my book.”

Ohhhhh Matt… Where do I begin? Yes, that qualifies, you’re right. But here are my observations, in no particular order: 1) The girl you met online wasn’t terribly “high energy?” Totally fine if there’s no chemistry, but what were you expecting, cartwheels? 2) What 23-year-old has online dating stories to compare? That’s ridiculous, like those women on The Bachelor who say they’re looking for a husband straight out of college. Be young! Worry about the other stuff later.

Thirdly, her passing out in your bathroom should’ve been her cue to leave, not sure how one recovers from that frankly. 4) Destruction of property, albeit gross and alcohol-driven, usually warrants a stealthy escape, that’s hardly shocking – even I’d support it 5) Your friend “accidentally” made out with her? Sounds suspect to me 6) Why is this chick all about bathrooms? And why do so many of these stories involve peeing, while we’re at it? 7) Sounds to me like whatever bar you found this girl in wasn’t exactly going to yield you any classy or high caliber of woman (Not that any bar will, in my opinion).

If someone were inclined to say “I told you so,” (which I’d never do, of course) they might say that’s what you get for not setting the bar higher. Just a thought for next time. I realize sometimes you just want to go out and have a little fun, but if you end up with a pee-soaked couch and swapping hook up stories with your friends about the same girl in the same night, probably don’t be surprised. Better luck next time, man!THAT’S WHAT SHE SAID

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After telling you about the awesomeness that is the Morrison Hotel Gallery yesterday, I thought it only appropriate to point you in the direction of something equally cool. For those who just can’t get enough of The Boss, you’re in luck. A new exhibit titled, From Asbury Park to the Promised Land: The Life and Music of Bruce Springsteen starts tomorrow. The exhibit will be featured at the National Constitution Center in Philadelphia and runs from February 17th until September 3rd.

The NCC is located at 525 Arch Street, Philadelphia, PA 19102 and tickets cost around $27 – a modest price to pay for any true Springsteen afficionado. It’s a great idea for a date, or just to revel in your own fan-dom. Whether you’re in NYC, PA or DC, it’s a relatively easy trip, if you’re so inclined.

According to the NCC, “This first major exhibition about the American songwriter takes a comprehensive look at Springsteen’s catalog, from such early bands such as Child, the Castiles and Steel Mill through his work with the E Street Band and as a solo artist. Visitors will have the rare opportunity to view more than 150 artifacts, including the Fender Esquire guitar from the cover of Born to Run, the outfit Springsteen wore on the cover of Born in the U.S.A., numerous handwritten lyric manuscripts, posters from all phases of his career, and various honors including his Academy Award for the song “Streets of Philadelphia.” In addition, the exhibition features Springsteen’s 1960 Chevrolet Corvette, which he purchased after the success of Born to Run.”

Sweet! Sign me up.GEEK WINGMAN

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So much has been written about Valentine’s Day that even the journalistically inclined are hard pressed to find a new way to tackle the subject. Taking the straight route, for example, dictates that we make some romantic comparison to a timely subject – like, oh…I don’t know…politics, as found here. Gosh, what a well-crafted argument, whoever wrote that must be pretty clever (or just shamefully self-promoting – your call).

Or there’s the statistical route, which isn’t flowery but still pretty damn interesting, like this compilation of cupid-related numbers. Eleven thousand children conceived on Valentine’s Day on average?! Ew, that’s more information than I needed…

But my personal favorite read as of late was about Valenswine’s Day, the day before Valentine’s when men take their mistresses out for a romantic tryst (hey, it’s better than double booking, right?)

This year, however, my contribution to the lovers melting pot is a 2012-themed Do’s and Don’ts list for both singles and couples. True, it may have been done before, but that doesn’t mean it’s not still fun.

For the attached:

DO try to avoid flaunting your syrupy sweet relationship details on Facebook or Twitter. Uploading excessive pictures of your gigantic floral arrangement or giving us the play by play of all of the things “the very best boyfriend/husband/fiancee in the whole world” did for you today tends to get on people’s nerves. Also, please try not to profess your love in 140 characters or less. The words “marry me” should never come with a hashtag in front of them, in my opinion.

Men: DON’T pawn off a gift that really serves your purposes as something you think we’d enjoy. I’ve said it before and I’ll say it again: giving lingerie and sports tickets is only altruistic if you’re dating Adriana Lima or Marv Albert. *Miss Wingman note - if you’re dating a woman who would love to hit up an NBA game on Valentine’s Day, marry her. She rocks.

DO recreate a fond memory with your beloved. If your first date was for Dim Sum in Chinatown and then a John Hughes revival at local theater, why not relive it? (And if it’s not possible, ordering in Chinese and Netflix’ing The Breakfast Club works, too).

DON’T be afraid to Do It Yourself for a gift. If you’re particularly good at something (cooking, playing music, etc.) now is a good time to showcase your skills. Just don’t go that route if you’re known for being notoriously cheap – homemade is endearing, but not if your reputation precedes you.

DON’T ignore the holiday entirely, even if your significant other swears that she hates Valentine’s and couldn’t care less about it. Fact: 53% of women say that they’d break up with someone if they didn’t receive a present on Valentine’s Day. So even if it’s just a card, give Cupid a nod. Or else.

For the unattached:

DON’T get drunk and text or call your ex. Likewise, don’t check their Facebook page or e-stalk them – it will not make you feel better – especially if they’ve moved onto someone else. The past is the past for a reason, leave it that way.

DON’T try to DTR (Define The Relationship) with someone with whom you’ve been casually hooking up. This is not to be confused with being DTF (Down To…you know), which everyone should be on Valentine’s Day. Right, Pauly D?

DO start fresh by eliminating painful reminders of your old flames on Facebook, G-chat or your mobile device (a clean slate is better than looking backward, after all), but DON’T do anything drastic, like overhauling your life. Joining every single dating website (and downloading dating apps), buying a whole new wardrobe and signing up for the next casting of The Bachelor is excessive, FYI.

DO turn the negative (read: a recent break up) into a positive. It turns out angst is great fuel for creativity, so find a way to channel it. Hey, it worked for Adele, didn’t it?

DON’T be a cliche. The idea of the embittered single female – or in rare cases, male – isn’t amusing, it’s just plain angry. Please avoid blasting “F*%k You” music or going to see a midnight showing of Carrie, it’s not helping your cause (or making the rest of us look good).

For both:

DON’T sext half naked (or worse) pictures of yourself to anyone, whether you’re in a relationship or not. Have we learned nothing from Anthony Weiner, people?

But DO spread the love. Remember how much fun Valentine’s Day was as a kid? You don’t have to write tiny cards to all of your coworkers, but dropping Hershey’s Kisses or conversation hearts on your neighbor’s desk is fun way to be nostalgic. Everybody loves a little kitsch once in a while, right?

And there you have it, Miss Wingman’s take on this hot button holiday. Sure, some may hate Valentine’s Day because it, following closely on the heels of the other dreaded singles holiday, New Year’s Eve, provides the one-two punch we can’t avoid. It’s like a tandem assault-by-calendar, if you choose to view it that way. But I’d prefer to think of it as just another opportunity to make someone else smile – and there’s nothing wrong with that. And, if you still can’t get behind it, just know that your own Valentine’s misery is probably nothing compared to this guy’s. My love to you all, today and always.THAT’S WHAT SHE SAID

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