Pre-Date Etiquette

10 May 2013
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Pre-date etiquette.  Is there such a thing?  For example – who does the asking out? Is it appropriate for women to ask men out?  Who plans the date?

As recently as when the baby boomer generation was dating there were universally understood “rules” and etiquette around dating, courtship and marriage.  Whether one followed those rules was their choice, however, they likely knew what they were.  Today – with the advent of technology, the feminist movement, blurred gender roles and expectations, alternative forms of “relationship” and a host of other societal factors – there do not seem to be universal rules to follow.  There is a lot of confusion in the world of dating and the daters I know are often seeking guidance.

I believe that anything goes these days. Women are far more independent than they were even 15 years ago and, as a result, are more confident going after what they want…including men.

In my experience, men are divided on this subject. Some men love an empowered and assertive woman who has the balls to ask them out and others would prefer to do the asking.

My only word of caution to the ladies who are comfortable initiating a date with a man is this: men are hard-wired to be the hunters…even those who say they are liberated and seem open to being asked out by a woman. If a man is dating two women simultaneously (or has just met two women of interest) and with one the traditional gender roles are more blurred, even if only on a subconscious level, he will naturally gravitate toward the less assertive woman in the long run…as a generalization.

Once a date has been arranged – who plans where to go, what to do?

Some people believe that whoever did the inviting should do the planning. Some people think that it should always be the man. There is no right or wrong. Each dater has their own set of values and expectations and the key is in communicating those. I have seen two dates (in the last month alone) go off the rails because of the way the plans were handled…or not handled.

If you are asked what you want to do on your date, be honest. Keep your language positive, maintain benefit of the doubt (you don’t know this person if it’s a first date, therefore assumptions are dangerous) and be flexible.

For example, you may say: “One of the reasons I was excited to go out with you is because I heard you’re really creative so I was looking forward to seeing how that translated into a wonderful first date. If you’re OK with it, surprise me – I’ll be happy to try anything you suggest” This politely tells the other person that you had an expectation and a preference, all while enhancing their self-esteem.

Or, you could say – when asked what kind of food you like: “I love anything except for Greek and Thai food and love trying new restaurants.” This gives your date some guidance and reassures them that you’re not the “whatever you like” type…that you’re flexible, but that you know what you want and you know what you don’t like…and you’re able to communicate that in a way that doesn’t make you sound difficult,  rigid or negative.

If you like to be the planner but are unsure if it’s appropriate, you could say something like: “Since we’re going out in my neighbourhood and you’ve been kind enough to offer to come to me, would it be easier if I choose where we go?”

Is it appropriate to go out for dinner on a first date?

I’m not a big fan of universal rules when it comes to dating. I think that what’s most important is that the people involved are comfortable and are able to act somewhat naturally. With that said, many active daters use the first meeting as an opportunity to assess physical chemistry and, therefore, like to have an “out” in case they’re not attracted to their date.

Dinner is typically a longer, more expensive commitment than grabbing a coffee, for example – so for this reason it’s become less and less popular as a first date option. People don’t want to be “stuck” across from a stranger until they’ve determined that they’re interested in them. Also, assuming the man is traditional and expects to be paying for the date, he may not want to spend money on someone he will never see again.

Despite this, there are still people who go for dinner on a first date and there’s nothing wrong with that. As mentioned, it boils down to personal preference, and what you’re comfortable with.

For those doing the asking, and/or the planning, just know that it’s not necessary to go overboard for a first date – it’s actually better that you don’t – and if you are inclined to suggest dinner, know that some of your dates will find that to be too much “pressure”…and, if that were to the be case, they would not likely tell you that’s how they’re feeling. Know your audience.

When going out on a first date should the man offer to pick the woman up at home? Should the woman let him?

I have had female clients go into a first date already with a bad taste in their mouth because the man did not offer to pick them up. I have had female clients ask me what was wrong with the men who did offer to pick them up and I’ve had confused male clients ask me what the proper etiquette is.

I think that first dates can be challenging for both men and women. It would be nice if both parties could have a genuine interest in ensuring that the other person will be comfortable wherever they go and however they get there. When planning and discussing the date, it can be as simple as saying: “I was going to suggest a cute little place that seems to be about halfway between you and me. I presume you would like to meet me there but am also happy to pick you up. Which is better for you?” This shows that the person has given the date some thought, that they are flexible, that they are sensitive to the other person’s sense of privacy and independence but that they are also willing to be traditional and chivalrous, if that’s the preference.

From a safety perspective, even for the most traditional daters, I do think it’s a good idea to meet your date in a public place until you’re comfortable with them….especially when you’ve met online. Be cautious of the false sense of security inherent in set-ups (i.e. family and friend endorsements), meeting people through “friends” on social media sites and drawn out pre-meeting communications. Just because your grandmother gave him a glowing recommendation (because it’s her bridge partner’s grandson) or because you have 27 mutual contacts on Facebook doesn’t mean that they are “good people”. You need to find out for yourself, and the best way to do that is to meet in public while preserving your privacy, and listening to your gut…always.

People are always asking me what to wear on a first date. It’s pretty simple. Wear something you’re comfortable in, bearing in mind that – contrary to popular belief – sexiness is a state of mind, not something you achieve via your wardrobe.  Wear something you’d wear to meet your date’s family or friends. Females – show a little skin, but not too much. If your legs are covered, show some shoulder, arms and/or MODEST cleavage. If your upper body is fully covered, wear a skirt.

Also, consider working with an Image Consultant (Sitting In A Tree offers this service) if you’re just getting back in to the dating game or if you feel your image/wardrobe could use a pick-me-up.  Men – this goes for you too!

If you have any “dating etiquette” questions, please feel free to e-mail them to:  We’ll consider answering them in a future blog.