Category Archives: Online Dating Basics

Online Dating Basics: Know Your Rights

A lot of the people I talk to seem easily frustrated by their dating website experiences. I often think that’s because they’re worrying about matters that really should not concern them. In this yenta’s opinion, some clarification is needed around some pretty basic issues. I’m drafting an Online Dating Charter of Rights so that we can all stop wasting time on the unproductive behaviours that lead to internet dating burnout.

Know your rights, ladies! You too, gents.

You have the right to remain silent. Opinions on the matter vary, but I don’t write back to people who don’t interest me. Not for myself, and not on behalf of my clients. Even if they seem really really nice, or have clearly taken some time to craft their message to you. On the few occasions I’ve bothered to write a nice let-down message, it’s bitten me in the ass and fast. Unless you think they’d be perfect for someone else you know, just don’t bother. It’ll save everyone time in the long run, even the person you’re rejecting. You also have the right to refuse to answer any question that makes you uncomfortable. You can choose to ignore it, or you can simply say, “I’d rather not share that with you right now, if you don’t mind” and carry on nicely, if you like everything else that’s happened so far. But you are never obligated to respond, ever.

You have the right to know what you like. Do you prefer tall women? Are you utterly opposed to dating a police officer? Do non-drinkers make you as nervous as raging alcoholics? Have you got lots of male friends with goatees, but couldn’t stand the thought of kissing one? Well, go right ahead and say it! There is utterly no point to being coy about these things. But make sure that you say it nicely, and not in the threatening “you’d better not send me a message if” fashion that so many people seem to employ online. Stating your preferences as a warning, like a bitter Buffalo border guard on the graveyard shift, doesn’t exactly invite others to get friendly with you. In my work I have sometimes avoided messaging potential matches because even though my clients did fit their criteria quite nicely, the way the candidate laid out his or her parameters was simply off-putting.

You have the right to expect a picture. There is absolutely no reason, at this point in history, for anyone to be ashamed of the fact that they are online dating. If you are, you probably shouldn’t be doing it. I don’t care if the person promises to send pictures later on. You’ve got a picture up, why don’t they? (Please tell me you have a picture up.) Worried their mom/boss/neighbour/ex is going to see it? Well, just what are they doing there themselves? Seriously, the people who don’t have pictures online – or who only share pictures of animals, cars, or cartoon characters – are hiding something. I don’t know what it is, but I guarantee you won’t like it. Don’t bother with these paranoid Luddites because they’re probably married anyway.

You have the right to change your mind. After one message, after three messages, after twelve. (Please don’t let it get to twelve messages before you meet somebody though. See below for more clarification.) You don’t have to answer any questions you don’t like. You don’t have to come up with excuses as to why you didn’t write back immediately, or jump on the offer of a meeting. It’s really important to trust your instincts when it comes to online dating. It’s not “shopping for people,” but when you’re at the pre-meeting stage, you are allowed to hit pause, rewind, or erase at any point. Most dating sites have a “hide” or “block” feature; use it if the person doesn’t take your backing away well. While it’s preferable to be upfront about it and not just disappear on someone you’ve been messaging, if they’ve done something to upset or offend you, you owe them nothing.

You have the right to request a meeting. If you’ve been messaging back and forth with someone, and things are going reasonably well, then it does not make sense to keep playing pen pals. Three messages sent and three received is about as many as I feel comfortable with before I start to get antsy, and too much literary foreplay can result in greater disappointment if the real-life encounter is a bust. Why wait? Unless your schedules are mutually very crazy, there’s no reason to prolong that coffee (even though you know I don’t suggest coffee). You’ve all heard of the Catfish thing by now, right? Well, this is just how it starts.

You have the right to keep looking. There is no such thing as “exclusively messaging.” Anyone who tries to glean whether you’re also chatting with other candidates – on the same site, or others you may be using – is best avoided. Even after you’ve met in person. I advise all of my clients to avoid any suggestion of exclusivity before at least a couple of weeks (and several good dates) have passed. (Note: this is true no matter what you personally get up to on a first date!) If the person you’re seeing immediately expects you to disable your profile – or does this to their own – after a successful meeting, I don’t think that’s a good sign. I think it’s needy, impetuous, and demonstrates a lack of discernment that could lead to relationship problems in the future. You both need to approach the situation with care, and taking yourself offline every time someone turns your head makes you seem flaky. It’ll be noticeable to other users, too.

I’m now opening the floor to comments. What other internet dating rights (or responsibilities) do people need to respect? And as always, be sure to visit to learn more about my work and available services.

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?

Online Dating Basics: Speak No Eejit, or What Not to Say on a 1st Date

"Is this your first time meet--"

When it comes to a first meeting, the old adage stands. Some things are better left unsaid. Here are a few examples that come up more often than you’d think:

1. “I thought you’d be _______er.”
Even if you think it’s a compliment. Just don’t.

2. “This is way better than I thought it would be!”
This sort of remark might meet with hearty head-nodding agreement if your companion is also “feeling it” in exactly the same way you are, at exactly the moment you say it. But otherwise, it’s the sort of statement that could dangle awkwardly in the air should the jukebox suddenly cut out. “Oh really? Well just how bad did you think it would be?”

It casts doubt on everyone’s motives for being there, and suggests a certain amount of frivolity on the part of the speaker. “What have I got to lose?” is of course the underlying mantra of everyone who takes a chance on love with a stranger – but let’s not say it out loud.

3. “Oh my god, don’t look now, but…”
Unless a famous celebrity has just walked into the room, there is no way that your date wants to hear the rest of this sentence. I don’t care if it’s your ex-wife’s mother’s secret lover who is cheating on her with your former high school basketball coach – and neither does your date. If you’re genuinely risking an encounter with the boss who thought you went home sick, or something similarly grave, simply say,

“Why don’t we take that table over there? It’s a little drafty by the door.”

Muster up some practical excuse as to why you need to turn the back of your sportcoat to the vengeful part-time model you dated for six weeks after college – the one who’s currently making a beeline for your part of the bar. Do not give the details, no matter how intriguing they may be, or may make you look. Protect yourself and your companion from any awkward encounters, but save the backstory for the speech you make at your engagement party. Your date will find it far funnier in the future.

4. “So why are you still single?”
See #1. Even if you think it’s a compliment.

5. “Do you mind if we split the bill?”
Whoever asks, pays. If that isn’t clearly happening by the time the check comes, just offer to pay – or say nothing and wait. If you’re desperate to escape, here’s what you do: settle your own tab privately with the server. Return to the table and say, “I’ve settled up and I’m going to take off – it was a pleasure meeting you – good night!”

There’s no point in quibbling over petty finances with someone you don’t want to see again. If you do – unless you’re truly interested in finding out right away how good or bad a tipper your companion is – bill-splitting just makes everyone look cheap, feel awkward, and reminds us all how badly our arithmetic skills have deteriorated since elementary school. Even if you’re not a well-off person. It’s a first date. If you can’t afford to pay for both of you (and you suggested the date), you might want to think of a free option next time.

Online Dating Basics: What’s in a (screen) name?

It’s the first thing a potential partner sees, before they’ve even clicked on your profile. It’s got to be good. So why are so many of them so bad?

No one old enough to remember The Sopranos (never mind The Godfather) wants to read that MobBoss4Ever is interested in taking them on a date. What if they give you a kiss at the end of the night?

RUthe14me007 has either feebly conceded that that six other people on the same dating site have already posed this hopeful question and doesn’t care – or decided to toss in a common Ian Fleming reference as an afterthought. (Possibly at the risk of alienating those who don’t care about the difference between shaken and stirred, or know a lazy allusion when they see one.)


We’re all capable of recognizing bad screen names. How do you make sure yours isn’t one of them? What does it take to create a good one?

1. Be witty. If comedy is part of your charm arsenal – and wordplay in particular – then by all means, come up with a clever name. Lines from films/tv, works of literature, songs or other pop culture references are acceptable – but try not to date yourself, or choose something indelibly associated with a cheesy character. No one wants to meet therealRonBurgundy, really.
Really. They don’t.

2. Be memorable. Long strings of digits or acronyms stress people out. You don’t want someone struggling to remember your profile. It’s hard enough keeping the passwords straight for three different social networks and two online dating sites. Why confuse people who may be too busy to commit complicated equations to memory? Type in your desired screen name. If every reasonable variation on it is taken, and you’re looking at adding numbers or letters, you may want to let it go – for it was never really yours, was it?

Oh look, REDNECKRAMPAGE69 wants to meet me! How enticing!

3. Be appealing. It’s tempting to resort to self-deprecation when putting yourself out there. While LoserInLove might be a name to which everyone else can relate, why make that negative association with your profile? If it’s the dark, rueful laughter of self-recognition you’re after, why not call yourself I’llDieAlone?

4. Be accurate. Don’t reveal your real name – certainly not your surname – but try to pick a persona that relates in some way to the content of your profile. Incorporate your interests or ideals, or a favourite activity. Don’t make it too broad – there are enough SportsGuys out there already. Choose something that resonates with you, or is likely to pique the curiosity of others. Refer to your passion or your job rather than your hair colour or your pet. A nuclear physicist will attract more appropriate partners with a screen name like AtomSmasher than they would with KittyLover.

5. Be smart. Or at least, look smart. Make sure everything’s spelled correctly. If Nietzchefan is already taken, don’t choose Neitzchefan instead. Avoid cutesy spellings. No adult looking for the real thing spells love l-u-v. Cut that out immediately.

Give your online persona a name that embodies at least two of these five characteristics, and any contacts you make will be much more likely to result in actual profile views. If you’re still confused, I’m offering a special summer screen name consultation – I’ll take a peek at your profile and produce 5 available names for $25. I’d be happy to help the first ten people who contact me. Don’t let your hastily-concocted combo of letters and numbers, cringe-inducing joke, or unintentionally suggestive first name – yes, I’m talking to you randy1974 – compel someone to delete your message before they’ve even seen your picture.

Online Dating Basics: Let’s (not) grab a coffee

"I hope I never see you again."

The classic first date may not be everyone’s cup of tea, and it doesn’t always create a successful encounter. Here’s why:

1. Starbucks has no atmosphere. The tables are too small, often occupied, and tucked away in weird arrangements because the bulk of the café floor is taken up by pop-up “standees” of cds, specialty teas, and cream, sugar and lid stations. The frantic climate created by long lines of java seekers is not one in which you want to be searching for a face you’ve never seen before in real life, either. While these places (and others like them) are popular choices for a first meeting simply because everyone knows where they are, it’s also jarring to enter a busy coffee shop with nothing but caffeine on your brain and encounter a person who stares at you intently upon arrival, with “Are you my date?” written all over them.

2. Not everyone drinks coffee. Or tea. Or hot chocolate. In fact, my own mother will not drink any beverage that is heated to a temperature above that of the average outdoor pool. That’s not to say she (or someone like her) couldn’t order a nice Orangina or something, but who decided that coffee was the ultimate no-pressure, easy escape beverage?

Why does the consumption of liquids at any temperature mean it’s a date?

Unless you’re going to use your tongue to tie a knot in your stir stick and impress your companion, you really could be anywhere.

3. Sit-down meetings feel like interviews. Particularly sit-down meetings with people you’ve never met before. You’re going to be more self-conscious about things like posture, whether your shirt is tucked in properly, whether your gut is hanging over your skinny jeans, what your hair is doing and – if you dare to order a snack – whether there’s something stuck in your teeth. You’re more likely to fidget, and you’re under a great deal more obligation to make and maintain eye contact. All of these factors add to your stress about the situation, and make you behave less like yourself. How is the conversation supposed to flow when you don’t even have anywhere else to look, except at the person sitting opposite you? (That’s if you’re lucky enough to get a table, of course.)

4. It requires no imagination. Seriously, from an evolutionary standpoint: as far as dating style goes, “Let’s meet for coffee” was probably the first great advancement that came along after grabbing your potential partner from behind and dragging her (or him) to your cave. Is that really all you can come up with?

5. There’s still only one exit. Just because coffee dates are traditionally short encounters – especially when there are no free refills on offer – it doesn’t mean beating a hasty retreat if you discover that you really don’t like your companion will be any easier. You’re going to have to meet your “cousin” somewhere in a half an hour no matter what – so why not do so after a walk by the busy waterfront, or a free mushroom identification lecture instead? And if things go well, and you decide to extend the date to another venue, well, you haven’t had coffee yet.