Category Archives: Ask Anne M.

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.

Ask Anne M.: Can style (or substance) opposites attract?

Carla Bruni-Sarkozy, until recently the First Lady of France, shows her rarely-seen frumpy side


I recently went on a date with a very attractive and nice woman. However, her style was a bit off and her shoes were very out-of-date as well as downright ugly (like… really bad).

I’m a very design-oriented, “artsy” and liberal guy, and her lack of aesthetic sense really turned me off. Even I was surprised at my reaction.

Am I being petty or too picky? Can an artsy person get along with an earthy person? Could a liberal be attracted to, and get along with, a conservative?


You raise a couple of significant issues, Picky Picky. First impressions, and the value we place on them consciously and unconsciously, have been the focus of decades of study by sociologists, psychologists, and marketing departments. I think it’s fair to say that anyone would be taken aback by someone whose appearance varied noticeably from our expectations of it. Such expectations are based on the subtle messaging about ourselves that clothing sends out to the world. If I’m told I hold the same values and goals in life as another person – at least “on paper” – and we’re of approximately the same generation, with similar interests, I’d kind of expect them to dress somewhat like me. Or at least provide a nice complement to my style.

You also describe her as attractive, however, which I assume means that underneath her dated duds she had an appealing figure at the very least. What you’re really gauging is the value of the person vs. the shell, and there is a difference. One study determined that when appraising new people, clothing has the most impact on social impressions, while person (including both face and body) dictates views of one’s athletic ability (and by extension, health). Interestingly, neither “costume” nor “person” exerts any notable influence over perceptions of intellect.

What you need to figure out is whether you seek certain attributes in potential partners because they will contribute to your long-term happiness, or because they have become preferences that are fixed for other reasons. But if you’re not sure, you might want to broaden your parameters a little, just as an experiment. Fashion choices, hairstyles, even taste in music are all easily updated. It’s whether you choose to view that as an opportunity (“Hey! Let’s go shopping together sometime!”) or a sign that something more significant is at play.

There are many reasons a person may appear to have given up on fashion, including practical, ethical, and financial ones. It’s entirely possible that your date is completely comfortable in her own skin, and uses her personality to put her best foot forward in the world rather than cool shoes. Or maybe she’s so much cooler and fashion-forward than you are that you failed to recognize her resurrection of the 90′s floral print Elaine dresses and penny loafers for the maverick move it was.

As mismatched couples go, style may well be more of an issue to grapple with than substance. Research into whether opposites truly do attract suggests that yes, it is very likely our mates will be drawn from a pool of people with whom we share certain attitudes – on everything from movies to politics to religion to a shared love of downhill skiing. But it is ultimately how well personalities complement each other that determines happiness. This means that yes, Picky Picky, a liberal and a conservative could technically fall in love and live happily ever after.

Mary Matalin, Republican, and James Carville, Democrat, married since 1993