Category Archives: Do’s And Don’ts

Correct Valentine’s Day Procedures for Couples and Singles

In case you’ve just awakened from a coma, or have not had electricity for some time, let me be the billionth person to remind you that Valentine’s Day - also known as Singles’ Awareness Day – is this Friday, February 14. I know this can be a high-pressure occasion for many people, coupled or single, and so I’ve come up with a few tips to ensure a successful observance – or non-observance – of the day:

1. Be happy – you’ve got it good! offers thorough selection of complicated V-Day sentiments

If you are part of a couple, take a moment to quietly savour that fact. The operative word here is QUIETLY. This is not “your special day.” This is a huge and profitable holiday, ranking second in spending behind Christmas and ahead of Mother’s Day in the U.S. A whopping $17 billion will be spent there this year alone. It’s an occasion that at least half the world marks and the other half has definitely heard of. It’s really not that special to you in particular. But if you’ve got someone who smiles at you when they haven’t seen you in a while, that’s some major warm fuzzy fodder right there. So go ahead and glow.

If you are not part of a couple, take a moment to quietly savour that fact. The operative word here is QUIETLY. This is not “it’s awesome / it sucks to be me” day. The world did not conspire to create this holiday so that you could gloat about how you don’t have to do anyone else’s dishes, and can kiss whoever you want, whenever you want, because you’re single. And if you do, those poor suckers who have to pretend to be excited about a short-stemmed roses from the grocery store that’ll be brown by Monday will simply tell themselves that you’re bitter and envious (ha!) Who wants to add to their smug (if delusional) satisfaction?

2. Be thrifty – get nasty!

66% of men and 30% of women would prefer sex to a store-bought gift

If you are part of a couple, and you don’t fancy feeding the retail monster just because the mall mafia tells you that’s what your partner wants you to do, but you’d still like to do something special, why not have sex? I’m not talking about making twee coupons you exchange for specific acts, or circus sex with props and costumes and special flavoured liquids. Just good old-fashioned, clothes-in-a-heap getting’ it on. Isn’t that why you’re part of a couple in the first place? Apparently that’s what two-thirds of men and one-third of women would prefer anyway, according to a recent survey. (I should note that I am personally slightly concerned about the big gender divide on this issue. Do you coupled-off guys need to brush up on your skills or what?)

If you are not part of a couple, congratulations! You don’t have to feed the retail monster just because the mall mafia tells you to do so. But if you’d still like to do something special, you can take even half of what the average coupled-off person expects to spend this year ($240!!!) and still buy yourself an extremely fancy high end sex toy. (For the record, I am NOT paid to endorse the Lelo brand – but I still very much do!) Or just go out to any bar – bars are NOT full of couples on Valentine’s Day, funnily enough – and enjoy the fire-sale atmosphere this not-very-important holiday creates. There’s sure to be at least a handful of very attractive, intelligent, charming people who have been had enough of scrolling through their coupled friends’ nauseating Facebook posts and just decided to hit the bottle hard. Why not take advantage?

3. Be Cupid – improve your karma!

Not feeling the love so strongly yourself this year? Pay it forward!

If you are part of a couple, and you know some single people who are looking for love, why not help them have a better Valentine’s Day? Throw a little party and invite them all (don’t tell them why – single people do not like knowing they are being set up). Encourage them to try online dating – OkCupid is a great free site that is also fun to use. If you don’t think you can project adequate enthusiasm for these tasks, send them my way!

If you are not part of a couple, and you know some single people who are looking for love, why not send them Valentines? Especially if you’re actually interested. V-Day was never originally intended for the happily coupled, incidentally. It was a day for secret admirers and clandestine couples (or wannabes) to declare their desires, not the “behold the happiness of my beloved and I, for it is majestic and overwhelming” parade that it is today. Everyone deserves a little love, even platonic friends, and no matter what anyone tells you, even an e-greeting is better than no greeting at all. I like someecards for its subtler grasp of the complex emotions these holidays elicit.

Still got a case of “the mean reds” about Singles’ Awareness Day? Here’s a personal inspirational tale:

In 1991, when I was living alone in NYC and kind of depressed at the age of 20 (I know – there oughta be a law) a friend sent me a dozen long-stemmed roses on February 14th. Once I got over the fear of being shot – nothing says “you’re about to die” quite like a giant Italian man pounding on your door unexpectedly, pointing a long white box at your peephole – I couldn’t have been more thrilled. In fact, I kept half of them and took the other six down to the rather legendary East Village bar that was right below my apartment, where another friend and I gave them away to total strangers and people bought us drinks all night. Until last year, when my boyfriend and I went to a dollar store and bought props to wear in the photo booth (total cost, including picture strips: $13), it remained my best V-Day ever!

Mrs. Robinson Replies: Five Ways to Handle Messages from Younger Men

Hollywood has long been enamoured of the older woman/younger man romantic scenario, but online dating sites are making it more plausible in the real world. If you’re a woman in your 30s – or 40s, 50s, 60s – you’ve probably received at least one message from a brash young man who wants to get with you. If you’re anything like my clients, you get them all the time. Some are shockingly straightforward, some considered and charming, some unabashedly pleading. How do you respond? Well, that depends on your reaction:

What kind of girl do you think I am?

If you’re not interested in casual sex with anyone of any age, you are well within your rights to ignore messages from randy wannabe boy-toys who are clearly – sometimes vividly – only interested in one thing. If the sender’s date of birth does not place him within your stated age parameters, you are under no obligation to respond at all. If the sender’s not wearing a shirt, and has composed a message of less than ten words or that does not form a complete sentence, delete the original message and just block the young buck. Any reply, even a firm denial of his advances, will only lead to even more insistent and lewd overtures.

You'd be so perfect for my friend/cousin/granddaughter!

If you’re flattered, but not interested, and can detect that a genuine gem of a guy lies behind the gesture, write back. Pleasantly acknowledge the fact that he’s got game – but make it clear that you’re not going to play with him. Just because you’re not buying what he’s selling doesn’t mean he should be taking himself out of circulation, though, and that does sometimes happen to guys who get tired of never receiving replies. (I read a lot of dating profiles. I feel for the fellas sometimes.) Plus, if he really is sincere about wanting to be with an older woman, he might be just right for one of your friends – or your daughter. It’s okay to let him know that it’s nice to be thought of as a viable option by someone of his generation, but you’re looking for someone with a little more mileage.

Sure, I could have babysat you, but there's no harm in writing back

So your interest is piqued by his picture or his prose, but you’ve never dared consider meeting someone in his particular demographic. Depending on the message and your moxie, you can write back taking any number of approaches. Let him know you’re mildly intrigued. (But only mildly.) Or challenge his interest in you directly, if you want to clarify his intentions. You can be as vague or explicit about it as you like. You’re not particularly invested in the exchange, why make it a big deal? You might refer to any number of pop culture touchstones when employing this tactic (“Is this a Graduate/Sex and the City fantasy you’re hoping to play out with me, or do you actually like John Coltrane too?”)

Okay, but this is a one-time deal

There’s nothing wrong with warm-blooded, free-willed individuals of any age getting together to satisfy one of the few truly universal human impulses. Who cares about the psychology behind the message when you haven’t been laid in (please insert whatever you consider a sufficient number of hours/days/months/years to qualify as too long)? There’s no need to be coy, but you don’t have to be crass, either. Reply briefly: “I’d be an idiot to turn down an offer like that, and mama didn’t raise no fool” might do nicely. Just make sure that both parties’ expectations are clearly outlined in subsequent messages. Arrange a brief meeting in a public place beforehand to ensure that he is who he says he is, and that his intentions are what he claims they are. A low-pressure, high-traffic outdoor venue (a park, a city square, outdoor market) is preferable to a sit-down meeting in a coffee shop where you might be spotted by someone either of you knows. You don’t want to have to pass him off as someone you’re mentoring (although that makes an excellent cover if you need one). When arranging intimate encounters, your Spidey Sense needs to be turned up to 11. It’s good practice to avoid traveling in a stranger’s vehicle, particularly if this is just a hook-up.

I'm old enough to be your... girlfriend?

Let’s say you’re willing to consider dating (much) younger men. OkCupid blogger Christian Rudder makes an eloquent case for the older woman/younger man scenario that is well worth reading. Some of the Gen Y types who approach my clients do appear to be sincerely interested in forging a relationship with an older woman. Many write eloquently about it in their messages and their profiles, and why not? Women typically outlive men by 5-6 years. Our more complex sexual responses see us aging differently in the bedroom than our male counterparts (and for us, it’s often more a matter of desire than physiological function). If you’re interested, and you do not discriminate against others on the basis of that which they cannot change, then you owe them the same consideration you’d show anyone else on the site. Don’t write back to the ones who say, “Wow, you’re a total GILF and I want to lick you all over.” But the ones who put real thought into a message – who have obviously read your profile, not just noted your age – deserve a thoughtful, flirtatious reply just like you’d send a chronological contemporary. Thank them for reaching out to you, and answer any questions they ask. Ask some questions of your own. What have you got to lose?

Ask Anne M.: Does playing The Dating Game make you a player?

Playful for Romance writes:

I met someone I’m really attracted to on Saturday. It was obvious the connection was mutual. Numbers were exchanged. On Sunday, we made a date for this Wednesday.

From the conversation, I know to be ready for more than just more conversation – but also that I would be remiss not to suggest a plant identification walk that evening.

The problem is, I have already invited two others who see me as housemate material, but who haven’t ruled out romance. Since taking up with someone around the same time as moving in with them seems unwise, I’ve been taking my time, deciding to see if the question of romance gets clarified one way or another.

"And now it's time to meet our three eligible bachelorettes - and heeeerrrrre they are!"

In that context, if both showed up, it could be easier to get a good sense of who likes who what way before the end of the summer comes and I am in need of a new address.

But to then show up with a date I’m definitely more into seems a bit much – and the lame-ass extrication of “something else came up” would be absolutely farcical. So I won’t be doing the latter, and see no way around risking the former.

The question then is: having created this potential mess, how do I handle myself?

Anne M. responds:

Playful for Romance seems a bit of an understatement, darling. Perhaps Fiercely Competitive might be a more appropriate moniker? Or Downright Greedy? We should all have problems like yours. Nice conundrum if you can get it!

I suspect you’re really nice, and that’s why you’re having a hard time with the fact that you’ve got yourself in this pickle. That makes it harder to give you the “tough love” treatment here. I hate to be so harsh, but I had to read your question three times to figure out even who was who. So what does that tell you? You’re probably not going to like my answer, because I don’t want you to handle yourself in a situation that you have definitely unnecessarily complicated. Sorry.

I’m not sure what your work or social circumstances are, but unless you’re an on-call transplant surgeon, I can’t excuse your deliberately double (or is it triple?) booking yourself for what should be a first proper date with this new person.

Just because you have the possibly perverse (but probably merely practical) desire to throw all these unsuspecting potential admirers into an impromptu speed dating situation doesn’t mean they should go along with it. Or be subjected to it unwittingly. First dates are hard enough without having to figure out who all the extra people are, never mind wonder why they’ve also been invited along. If I were your date, I’d probably assume you regretted having asked me out individually, or fret that I’d misread your friendly intentions as romantic interest.

If you follow through with this plan, at least one of them is going to figure out what’s happening while it’s happening. And then you will be toast, likely with all of them. I’m not even going to bother doing the research here. This one’s pure instinct. Without an incredible poker face and very finely honed social/diplomatic skills, you’re going home empty-handed – or worse, in the company of someone who is so insecure or used to being treated inconsiderately that they don’t even realize they deserve your full and undivided attention.

You need to stick to the original plan you had with the two potential housemates, and you need to tell the new candidate that you misspoke when you suggested Wednesday. (Or agreed to it – I’m not sure who proposed that specific date.) Having had a look at your schedule, it turns out Thursday, Friday, Saturday, or even Sunday might be better. Don’t let it go past the one-week mark, though.

If you really like the idea of the plant-identification walk, then just do it again. And you’ll be just as excited about it as you were the first time – but better. You’ll have had a rehearsal, at least.

"Okay Miss Playful, it's time to choose a bachelor!"

Unless you’re planning some sort of modern ménage à trois, I’d also advise you to figure out as quickly as possible which of your future housemate possibilities intrigues you the most, and take care of that situation before you move in. Because otherwise, you’re being really sneaky already, and that’s not a good quality in someone with whom you’re going to share a living space.

This isn’t a game show, and it isn’t all about you. Stop playing around, sort out your schedule, and despite the myriad of options that may be before you, take them on one at a time, please.

There will be plenty of opportunity to complicate things later, and it sounds like you’re more than up to that challenge!

Ask Anne M.: Do good dates come to those who wait?

"Message me. Adore me. OBEY!"


I recently joined a dating website, and my best friend and others assure me the best approach is never to make the first move. Not even a wink. What are your thoughts about a woman making the first move in an online dating environment?

ANNE M. responds:

Wow, New to the Game, that’s strange advice. I’d be curious as to where this sage wisdom is coming from. The happily married? Someone who’s never online dated? Let’s set aside traditional patriarchal gender roles for a moment (I’m no big fan of them anyway). If this sit-back-and-wait approach had any value, how would gay men and lesbians ever meet each other on dating sites? As my very smart (and happily married) friend Elisa says, “You want something? You go get it. Online dating is passive and remote enough without imposing arbitrary rules of engagement.”

I couldn’t agree more. When you do so, you risk never hearing from the type of people you really want to meet. If just staring at a particularly appealing profile yielded results, no one would need my services. People who are serious about meeting someone take action. I know it’s hard. Society doesn’t encourage women to be romantically assertive. Regardless, for the sake of potentially emboldening shy types everywhere – regardless of gender or sexual orientation – I will share the following observations:

1. Simply knowing that someone finds you attractive makes them more attractive to you. Maybe not in the same way – at least not at first – but it does tend to at least pique one’s curiosity about a person to find out that they’re into you. Because even if you thought they were a total social write-off before you had that information, you now know one rock-solid truth about them: they have excellent taste in you. (For those of you who love studies as much as I do, there is research to back up my assertion.)

Online dating is passive and remote enough without imposing arbitrary rules of engagement.

I remember once getting a rose in high school, through some student-council sponsored exchange that delivered stems to lucky recipients in their home rooms on Valentine’s Day. The guy who’d sent mine was someone I knew by name only – he was a little older and we shared a class because I was fast-tracking to graduate early. He was smart, presentable, friendly and well-spoken, but had previously made no impression on me. Yet that day in class, I couldn’t help but notice all sorts of things I’d never seen before. Like his really nice arms, and really blue eyes… and although it didn’t turn into a great romance, I did go out with him a few times. That never would have happened had he not been confident enough to express his interest.

2. Men are surprised, but not unpleasantly surprised, when a woman makes the first move. If you visit any of the numerous forums in which men discuss their online dating woes (and believe me, they are agonizing about this stuff just as much as you are) you will find that most of them report very few females initiating contact. But almost all of the men weighing in on the topic suggest that they’d love it if that happened more frequently. Nearly universally they express that unless there’s something really wrong with the sender’s profile, they would respond to the message at the very least. When I used to work for a high-end matchmaking agency, male clients were always thrilled if I told them that the woman I’d matched them with wished to call first (rather than the other way around).

It might also be a useful empathy-building exercise to try messaging someone who hasn’t sent one to you first. Because isn’t that the huge (and potentially humiliating) risk a man takes every time he initiates contact with you? The absolute cornucopia of information that is oktrends has even mined okCupid user data to identify some of the most effective things to write in a first message, if you’re stumped.

3. Online dating is supposed to be fun. Why not try something different? You’re able to make moves on the Internet that would be difficult to pull off in a face-to-face or even telephone conversation. There’s room to breathe, think about things before you write them – particularly if you’re not instant messaging. Embrace the experience. Make the most of it. You’re online because you want to date. Flirt, smile, wink, message. Put yourself out there. Otherwise, you and that great guy whose friends also gave him this nugget of wisdom will keep circling, but never meet.

A little courtesy goes a long way

If your grandmother is (or was) anything like mine, you’d have a hard time getting her to understand how to open an email attachment. So the idea of turning to her for online dating tips might seem preposterous. But if you apply one of her most basic pieces of advice – “Mind your manners” – to just about any online situation, you’re going to get better results. And if you get the chance to test your virtual success by meeting one of your matches in the real world, I hope you’ll bear at least the standard Emily Post wisdom in mind.

But before you even get to that stage, you’ve got to line up dates. And despite your best efforts, they may not always go so well. Here’s an example:

Let’s-Call-Her-Alice had been dating women she’d met on popular free sites like OkCupid and POF for a few months when she went out for a meal (hint: not a good first date) with Let’s-Call-Her-Jamie. As is often the case, they spent the first several minutes discussing their respective internet dating misadventures – and their relief that at the very least, both of them seemed to be reasonably well-groomed adults who resembled their pictures quite closely. Then Alice raised the obvious question: why were they both still single?

Jamie started crying. Not just a little teardrop in the corner of the eye, or a quaver in the voice. Full on crying. Alice thought it was a joke at first. Then, when she realized she’d triggered something major, she offered a hanky. Just like Grandma (or Grandpa, if he was the right kind of manly) would have done. Then, twenty minutes later – with Jamie still carrying on, seemingly inconsolable – she left.

That night, she went home to close her two online dating accounts, determined never again to waste her time and money on a real life encounter with a freak she’d met on the Internet. Then she looked in her inbox, and realized that she still had another date scheduled. For the following afternoon.

Jamie started crying. Not just a little teardrop in the corner of the eye, or a quaver in the voice. Full on crying.

Desperate though she was to cancel, she realized that it would be the height of rudeness to do so on such short notice. And besides, her prospective date had a very cute picture. So she put her game face and date makeup on, and braced herself for another grim reminder that the only thing worse than a lifetime of loneliness was an hour of craziness. If only she’d met crying Jamie a day earlier, she could have begged off. But less than 12 hours is unacceptable except in cases of emergency, and Alice is a person of conscience.

And had she canceled, Alice would never have met Let’s-Call-Her-Tracy. And when they did meet, even though she had a really really really great horror story to tell – she sat on it.

(Because  talking about bad dates – even though it’s something to which all online romance seekers can relate – is bad etiquette if you’re hoping to have a good date, in my professional opinion. At least, right out of the gate it is.)

Plus, Tracy was even cuter than her picture. And she laughed a whole lot harder at that story when she finally heard it – at their engagement party.

A little courtesy goes a long way, lovers – and in all kinds of ways you could never predict. Be nice to each other every chance you get.