How to Orchestrate the Perfect First Date — how to ask ’em out, how to plan it, what to do, where to go, etc

Posted by W. Shane Duquette
Filed under Blog, Dating

So there are the classic dates. You know, like dinner and a movie. Or going out for coffee or drinks. Those are fine… kind of. They’ve got a lot of downsides and they aren’t that incredible in and of themselves, but sometimes you and your date are interesting enough for that not to matter. If the chemistry’s right the date itself doesn’t need to be super grand, sure, but why not have a grand date anyway. It makes things so much easier and so much more fun. Makes for a much more interesting first date story too.

So how do you it? By scheming up something creative? Here’s one reason not to: as soon as people put on their romantic thinking caps they all come up with the same “unique” ideas (like glow-in-the-dark mini-putt) and the dates usually end up being as unoriginal as ever but in a contrived and unnatural kind of way. I’ve had much better luck on the dates where I just do the things I love doing. That sounds like terrible advice that doesn’t actually work, like when the hot girl you have a crush on tells you to “just be yourself” while she goes off and dates some jerk you’re jealous of — that’s not what I’m saying. There’s a method here. And a way to let your individuality come through without having to contrive up some super-unique dating strategy. This is what I call the spontaneous multi-date. It took me years of dating and hundreds of first dates (thank you Myspace) to figure out how simple it is. This is what I believe NATURALLY occurs on the best of dates with the coolest of people. I’ll go over it from start to finish… but first let’s start at the beginning.

How to Get a Date

Books have been written on this that still don’t cover even half of what I wish I knew. I’m not going to go into much detail. You can meet girls through your friend circle (but please limit yourself to 1 girl per group of friends!), you can meet girls at school, at work, on the street, at the book store (bonus points) and through your social activities and hobbies. If you have a life you’ll meet a lot of girls without needing to do anything out of the ordinary. Alternatively, every rad girl I’ve ever dated has been to a night club at some point in her life, so great quality people DO go out to them. And, oddly enough, the internet is full of really great people that can’t find anyone as great as them and thus resort to online dating. There are lots of incredible guys and girls online. It isn’t just full of weirdos that can’t get a date… it’s also full of perfect 10s that can’t find other perfect 10s in their day-to-day lives. If you want more dates give it a try. It works great. Here are two great sites that work wonderfully: Plenty of Fish (more popular) and OkCupid (more fun/functional)

How to Ask Your Date-to-Be Out

Saying “Hey we should hang out sometime” won’t get you a date unless the other person is really keen and willing to take charge. You can throw it out as a feeler and see what they say… but why bother? If they say yes you still don’t have a date. You maybe have a date sometime doing something undetermined. You’re not much further along than where you started. Worst of all, you’re putting the burden of the next step on them, and even if they do want to date you it may very well be a burden that they don’t want. Here are three ways to get a solid answer without placing any burden on your would-be-date.

The common interest: If you’re chatting with someone you dig and oh my god you both just happen to love indie rock you’ve got the perfect opportunity. You say “hey, there’s this great indie rock band playing Thursday night at Zaphod’s. You game?” Or even “hey there’s this great bar in my neighborhood that plays rad music. We should go grab a drink.” Most common interests can be turned into some sort of date… but if it turns out you both love the same sort of movie I’d put that in your pocket and save it for later. That’s great for a second phase 2.

No bullshit: I’m pretty forward. There’s nothing wrong with cutting out the pretenses and saying “hey you seem cool. What are you doing Thursday?” If they’re curious about you or  like you a bit already this is a great way to go. I prefer this route. And the benefit here is if they say yes… you’ve taken the lead and can take them out to do whatever you want. This is good, because after this article you’ll probably be better at planning a date than they are 😉

The Gladiator Arena: throw a party / go to a party. Invite all the people you’re romantically interested in. See who wins. This one is fun. Or, of course, you can just invite one girl — but where’s the fun in that?! The line to use? “Hey, I’m having some people over on Saturday. It’s going to be a blast. You should come! Bring friends if you like.” This isn’t technically a date… which means that you aren’t actually an asshole inviting 10 dates over… so I figure that makes it Kosher. And I really enjoy it. Alternatively, the arena date makes a great second date (but inviting all of your second dates over at once is a bad idea). If it’s officially a date I’d just invite the one. If it’s ambiguous enough invite a dozen if you want. This works especially well if you’re the type to accumulate a lot of phone numbers while out and about. You don’t know if you like them romantically — you just know that they seem like cool fun people. Invite a bunch over along with your friends and see what happens.

Prepping for the Perfect Date:

You don’t need to plan out a rigid static date from start to finish. Hell, if you’re a popular organized person living in a cool location with a lot of awesome plans all the time you probably don’t need to do ANY prep-work whatsoever. But just incase you aren’t you might need to do some research beforehand. I used to. Now I just schedule drinks and go with the flow. There are lots of fun places in my neighborhood, I’ve got lots to do at my place, and my friends are great people that are always up to something interesting. Something fun always happens.

1. What do you want to happen? If you want to go back to her place you should plan something near her place. If you know she loves James Bond movies and you’ve got 20 of them at home you should plan the date near your place so you can go back and watch them afterwards. If you want to pick her up and drop her off, you’d better not plan to drink. If you want her to subway home, you need to make sure she gets on before they stop running. Assume she ends up being incredible and figure out your ideal end of the date, whether it’s that night or the next morning. Plan for the best-case scenario. And clean your room.

2. Know the night / know the city: Do some research. Find out what your friends are doing. See what parties are going on. Find out what bands are playing at the local bars. Find out what clubs are happening. Know what movies are playing.

The Ultimate Date: The Spontaneous Multi-Date.

Phase 1: The Icebreaker

Meet at a casual place so you can get to know each other for a bit before you really kick things off. Coffee, tea or drinks are ideal. Hell, even Bubble Tea works. Here’s why:

First, unless you’ve known the person for a very long time and you know the date is going to go great… you need an escape plan. I like to grab a drink at a bar near my house that I love. 45 minutes into the date if I’m not having fun I can say “hey, it was great meeting you, but I’ve got to jet!”

Second, you need to give THEM an escape plan. It can be stressful to be asked out on a date that’s going to last 5 hours. Dinner and a movie? That’s a LONG date. If within the first fifteen minutes you realize you don’t like them you’re screwed. But if you get asked out for a quick drink well there really isn’t much to lose. It makes it easy for them. They can leave whenever they want. No pressure. No stress. No expectations.

Third, it’s a great way to chat and get warmed up before moving on to other things. Either you’ll be feeling good from the caffeine in the coffee, the alcohol in the drinks or the… sugar(?) in the Bubble Tea…. I don’t know anything about Bubble Tea.

I often go on dates with girls that are really nervous. The first thing you’ve got to do is make sure that your date is feeling comfortable. You’re hosting the date so in a way it’s almost your responsibility to make sure they’re taken care of. You should expect to need to lead the first part of the interaction, as they might be shy. You can take charge of the conversation or try and get them laughing early, which is often disastrous for me because I’m really really damn bad at telling jokes… but that usually does the trick, because then they get to laugh at my bumbling sense of humour, which eases their nerves. If YOU are the nervous one, well, worse things could happen. Try not to be, but don’t be embarrassed about it either. Some of the best dates I’ve had have been with girls that were terrified initially. I don’t like ’em any less because of it. I mean, I AM pretty terrifying.

What do you talk about? Talk about things you’d read in Cosmo or GQ and you’ll be fine. No need to bring up politics or past relationships yet. Keep things light and fun. Find out about their friends and family. Things that you guys enjoy. Tease for bonus points but don’t make them cry. Possible topics:

-Future ambitions
-Fun traveling experiences
-Something you read in a magazine
-Talk about their best friends. Or yours.
-Relationships of the best friends
-Talk about families
-Worst date (playfully)
-Most embarrassing experiences
-Would you rather
-Never have I ever
-Truth or dare

If you get a really shy date you can get fake or cursory input from them and continue on with your monologue until they warm up. Just launch into a story and ask a lot of questions. If they keep giving one word answers just keep going until you warm them up and something hooks. Sometimes you’ve got to kind of just keep talking until you land a question that they can sink their teeth into. My female friends often encounter guys that don’t talk much on first dates, so as a guy it’s a good way to stand out… and as a girl it helps to have some tricks up your sleeve to coax out some personality.

A common mistake is to talk and talk without asking questions. You’ve got to present them with opportunities to voice their opinion. The end goal is to get them to open up, have a good time and be comfortable around you, not to have them listen to some diatribe about some issue you’re having. I could probably sit at a deserted bar all alone and the conversation would be just fine. I can talk and talk and talk without much input—but that would get really boring really fast. Dynamic conversations with witty back and forth banter are far more entertaining. Don’t hog the airspace.

Conversely, don’t be the asshole that makes the other person carry the conversation. You should come armed with an interesting arsenal of passions, knowledge and interests that you can bust out at any time. Not like an encyclopedia, but more like an interesting person that does interesting things and thus has interesting things to say. You need to contribute in some way. If you notice the other person ADORES talking you can contribute by actively listening and saying things like “wow that’s really interesting, keep going”. Don’t, however, use that as an excuse to keep someone that would prefer a balanced conversation in the driver’s seat.

If you want some conversational ammo here are three books that I found fascinating and that often spark really interesting conversations: Outliers, The Four Hour Body, Freakonomics, and The Origins of Virtue.

You can also check out TED for great video lectures, read pop culture magazines, pop culture websites (like digg), or… well. I have to admit I don’t do this one, but I’ve heard the news can be a good thing to read as well.

Ooo and this is bad. My girlfriend likes to say “So… Tell me a story”. Don’t do that. It’s so vague and open-ended that it becomes really @$%& damn hard to answer. I managed to whip out some good stories the first few times but she just keeps asking! I do plan to master answering the damn question because I really doubt the little fiend will stop asking it and she’s just so cute when she does… but don’t impose that burden on your date unless you’re trying to test them.

So when the conversation’s going well and you decide you don’t want to end the date at drinks, it’s time to do something else. Grab the bill and say “Come on. Let’s go.” You can add in something like “there’s a really cool party going on down the street. Let’s check it out. You’ll like it.” Or you can make it a surprise. Here are two subtleties you need to keep in mind:
a) Move on at the high. When she laughs at my joke and I feel all proud of myself and think “hah she likes my jokes. I like her”… that’s when I’ll move on. When you decide things are going well leave then. Don’t wait for things to go stale. If things are starting to get a little dull why would they want to keep hanging out with you? When things are at their best move on and they’ll remember the phase 1 with how it ended: perfectly.
b) You invited them out, so you grab the bill. It isn’t a feminism or anti-feminism thing. Whether you’re a boy or a girl grab the bill. If the other person offers to pay you can either let them or say “Oh it’s fine don’t sweat it.” I like to have cash so I can just toss it down and leave. It shouldn’t be a big deal. Besides, it’ll only be a few dollars: it’s just drinks. If you can do it without them noticing it’s even better (although I’ve had dates accuse me of dining and dashing). And tip well. If you can’t afford to pay for both you and your date and leave a good tip that’s fine: do something free instead. The bars I like are dirt cheap so it really only ever is a couple dollars… but ‘er that doesn’t stop me from bringing models on a diet who drove to come see me to a bar that they obviously can’t eat or drink anything at? Oops. Don’t do that.

Phase 2: The Spontaneous Adventure Date

So you’re having a great time, you’ve paid the bill, and you’ve just said “come on, let’s go.” Before they say anything you can hold out your hand and hopefully they’ll take it. This isn’t, of course, necessary, but if I like a girl I usually like to hold her hand and I think it’s a great way to communicate “come with me. I’ll take care of you. Don’t worry.” while your confident grin communicates “you really don’t want to say no to me right now because this will be a lot of fun.” (after a few beers it might be hard to master those subtleties but do your best). Some people get confused — this isn’t the time to hold her hand like she’s your girlfriend. It’s the time to hold her hand, see how it feels, see how you like it… and then let it go. There’s plenty of time for more of that later. Two steps forward one step back.

So where do you take her?! This is where your research comes in. Feel the mood out. And, of course, feel free to be spontaneous. Being spontaneous is always easier when you have options though—so have options.
-If you’re full of energy and it’s 11pm you can hop down the block to a club and go dancing
-If you guys are feeling relaxed you can jet back home and watch one of those James Bond movies you’ve both said you love
-If your friends are out partying you can go meet up with them
-If there’s a wicked band playing down the street go check ’em out
-If you’re having people over jet back to your place
-If you want more to drink head home and serve ’em flaming sambuca shots (and throw on a fog machine)

I’m a rocker that likes to drink, dance and listen to live music… so my examples fit what I like to do on any given night. You can really do ANYTHING. It doesn’t need to be anything special or unique. You can take them to Shoppers Drug Mart and pick out deodorant. I did that once and had a lot of fun. I picked out some pretty rad deodorant too. I wasn’t a fan of Old Spice but they’ve got some good scents out right now. Point being: do something you’d want to do with or without her and well, then it can’t not be fun, right?

You can have as many Phase 2’s as you want. Go to three parties and a club. After the bar have a couple drinks at your place and then go out dancing. Each one of the events, in a way, counts as a different date. This is great because you get to know each other really well really fast in a variety of different situations. And the whole point of dating is to decide whether or not you like the girl deep down and in a variety of situations, right? The night is action packed and full of adventure and things never have time to get dull. Just remember caveat A from the previous phase: end each event on a high.

Phase 3: The After-Party

This one is really up to you. I’m not one to say that you should sleep with a girl 7 hours after meeting her (the pick-up-artist standard) or that you shouldn’t. If you want to sleep with a girl on the first date then go for it. Plan your last Phase 2 date at a location near your place and bring her back. Alternatively, plan it at a location near THEIR place and let them take you back. If, like me, you’d usually rather save it for another time, that’s perfectly fine too. But I’d recommend cleaning your room and being prepared for anything anyway. You never know what could happen… and if a kid happens, well, that’d probably be bad. So be prepared.

Of course, nothing says that going home with them means you need to seal the deal in any sort of way and it doesn’t mean that they’ve agreed to anything either. Don’t be pushy. Don’t ever pressure her into doing anything (and especially not into sleeping with you) and respect the other person’s boundaries and wishes.

When the date’s over you can take them back, go to their place, drop them at a cab, drive them home, drop them at their car or walk them to the nearest public transport stop and wait with them. If you’re a guy you need to keep them safe, so keep that in mind. A girl should never feel scared or worried around you and she should always feel free to leave at any time guilt free. This applies to the small details too. Just because you aren’t scared of the crack addict hobbling down the street doesn’t mean you shouldn’t put her on the other side of you so that she doesn’t need to be the one passing next to him. And your neighborhood might feel safe to you at night, but there’s no reason to make her scurry through it alone on her way home. Don’t just keep her safe, make sure she FEELS safe. And don’t just keep her feeling safe, make sure she actually IS safe, too.

Phase 4: Going for Round 2

You don’t need to wait 3 days after the date to contact her. Hell, you can even schedule a second date halfway through the first date if you guys are really getting along. You don’t need to be sneaky about the question, either. A simple “I’m having a great time with you. I want to see you again. What are you doing Thursday?” works fine. If you don’t want a relationship watch out about seeing them too often, or you guys are liable to get attached. Once a week is a good benchmark if you want to keep things casual. If you don’t mind if things progress into a relationship feel free to see them more—but not in a needy or clingy way. Don’t go breaking plans with friends or ditching your hobbies in order to fit into her schedule. You don’t need to have imaginary obligations or pretend to be busy either though. I’ve gone on second dates the very next day (and third dates the day after), and I’ve gone weeks without seeing a girl I’m rather interested in. Either way works. Once a week really is a great starting point though.

The Physical Side of the First Date:

You can kiss her in the second minute or on the second date. You can wait 5 hours or 5 years before having sex with a girl. That’s all up to you and your date. What you CAN’T do though is get lost. If you have a date and you haven’t touched her or flirted with her you haven’t really had much of a date. That’s a great way to keep things platonic. I wouldn’t recommend trying for sex before kissing her unless you know what you’re doing and want to try something different. Kissing her out of the blue before you’re comfortable holding her can be an awkward event as well. If you seem “lost” they’ll sense the awkwardness, so it helps to know how things usually go down. Here’s how it often works for me:

0) No touching. If you don’t like them romantically then don’t touch them. That will send the right message. If you do like her but you’re a wimp then you’ve got a problem, because you’ll be communicating that you’re just a friend… or even worse: a wimp.
1) Casual touching. This happens naturally for most people. If you like someone there’s nothing wrong with touching their arm or guiding them with the small of their back. You’ll notice that when there’s chemistry between two people they end up closer to one another and during natural conversation they’ll end up touching one another. Picture a girl saying, with a big half-offended grin on her face “oh you jerk you! I can’t believe you said that!” while reaching out and playfully hitting you. This is good. If it doesn’t come naturally to you that’s fine. You can cheat. Just learn to read palms.
2) Cute touching: Lead them around by taking their hand. Hug them if they say something adorable. Rest your hand on them. Play with their hair. This is the type of touching that happens naturally with people that like each other AND are comfortable with one another. Up until you’re physically comfortable with one another I don’t think you have any business kissing someone—unless you really know what you’re doing. There are tons of exceptions and if you have a good intuition with things like that you can play it by ear. Don’t do the “oh God I like her should I kiss her? I haven’t touched her or anything I wonder if she likes me maybe I should kiss her” thing. If you aren’t sure take it step by step and get comfortable physically first.
3) Kissing: I kiss a girl when I really can’t resist her any longer. Oftentimes the more I like a girl the longer I’ll wait, because I know that since the tension is so high it will be incredible. Some of the best kisses I’ve had have been really late kisses. This doesn’t mean you can be a wussbag. If you’re TOO CHICKEN to go for the kiss they’ll know. That’s bad. I waited many hours after the kiss normally would have happened recently and had to say “haha I know what you’re doing and I’m not going to kiss you” because it was so clear that a kiss should be happening right then. Saying “Oo are you going to kiss me?” when you see them trying to go for it is fine too, but be prepared for some backlash. You might get a “Pff” and a slap. You’re also allowed to ask. You can say “Do you want to kiss me?” Yes means do it, maybe means you say “Okay, well, let’s find out” and you do it, and no means no, but then you can always say “good, because I wouldn’t have let you ;)”
You don’t need to be all nervous about kissing. You can joke about it. You can do it early. You can do it late. There’s no reason to freak out about it.
How do you know when the other person’s ready? The easiest and most obvious way is when their face ends up really close to yours while you’re talking. People’s faces get closer together subconsciously when they’re gunning for a kiss. The other rule is the three second rule. If they stare into your eyes for three seconds without saying anything you can kiss them. This even works sometimes if it’s an angry stare, believe it or not. I went through a phase where most of my first kisses would spring out of a girl giving me an angry stare.
4) Tonguing: What I mean by kissing is the cute stuff. What I mean by tonguing is the passionate racy stuff. Necking is included here. So is ear nibbling and body kisses. When you do this beware: it escalates things quickly. I’d recommend staying away from too much of it in public places. It’s fine to do it a bit, but be ready to push ‘er off when things get to be too much for the location you’re in. What you don’t want to do is get all hot and bothered in a public place, not be able to escalate any further, have the sexual tension be completely used up, and then feel all sleazy about it afterwards. If you’re in a private place do whatever you like.
5) The Sexy Stuff: I won’t go into this much here. Once you start passionately kissing this has always seemed to take care of itself. If you’re a boy though you should know how to undo a bra strap with one hand ambidextrously. If you can’t that’s fine, but be ready to laugh about it when she notices that she’s the first girl you’ve ever undressed.
When the clothes come off I don’t care how ugly you are—you need to be confident. Sure, maybe you should have started going to the gym 4 months ago, but it’s too late for that now. You’ve got to flaunt what you’ve got. Don’t try and hide your pot belly by turning off the lights and wrapping it in sheets (I’ve seen this done). Be groomed the way you want to be, but if you’ve forgotten to be who cares. I’ve uncovered enormous scars, hidden flabs, jungles, prickles, you name it. I’ve never really cared. Really, it doesn’t matter. And if something goes wrong that’s fine. Don’t freak out about it or get all serious. If you give them a bloody nose or encounter… other blood flow issues… just handle it gracefully or humorously and that’s what they’ll remember: that you can handle yourself well in compromising situations. Try not to dwell on it.

To conclude:

Be the you that you are around your friends or your little sister. Don’t be the wussbag or player that comes out when you’re around an attractive girl. “Just be yourself” is terrible advice but “be the confident person you are around people you’re really comfortable with” is great advice. Some guys put on a pick-up persona. These are the guys that drive by in their car saying “hey baby where’s the party at? Want to come for a ride?” Just drop the facades and have fun in a confident and comfortable way. You don’t need to talk like a player, a cocky asshole, a stand-offish diva, a servant or like a shy nervous little kid. This is why it’s important to go on dates—so that you build up that natural comfort and confidence with them. That way, when the right person comes along, you’re ready. I think it’s naive to think that your love life will just magically work out. I put a lot of effort into mine and it’s always paid off for me. I date rather often, I’m completely comfortable doing it, I have a blast even if I don’t end up in love with the girl, and I’ve had great girlfriends in the past that have treated me wonderfully. And I couldn’t be happier with my current love life. It’s all worked out and I’m sure it will continue to. But I didn’t just wait around watching Gossip Girl on TV and waiting for it to happen.

Tuesday, March 1st, 2011
9 Responses to “How to Orchestrate the Perfect First Date — how to ask ’em out, how to plan it, what to do, where to go, etc”
  1. Christopher Cheong
    March 4th, 2011
    3:08 pm

    This is beautiful, I am now ready to get the ladies. Thank you FH for making me a charmer


  2. Jessica Rudnicki
    March 5th, 2011
    7:25 pm

    Great advice, Shane. Any guy or girl will get tons of value from reading your tips. Keep it up!


  3. Chris
    March 11th, 2011
    4:06 pm

    “You can say “Do you want to kiss me?” Yes means do it, maybe means you say “Okay, well, let’s find out” and you do it, and no means no, but then you can always say “good, because I wouldn’t have let you ;)” …

    Looks like someone has read “The Game”

    Haha, seriously though, don’t stop blogging your posts rule.


  4. W. Shane Duquette
    March 11th, 2011
    6:45 pm

    Hahah yeah I’m a big fan of Neil Strauss. He was one of Tim Ferriss’ test cases in his new book. Apparently now he’s buff 😉


  5. Josue Sawdo
    May 26th, 2011
    11:36 am

    Well done, and well put.


  6. v-mart
    January 31st, 2013
    7:28 pm

    Very good article! one of the best written and truest facts on the topic of dating and relationships. Really opened my eyes to stuff I was/wasn’t doing. thank you!!


  7. W. Shane Duquette
    April 23rd, 2013
    3:00 pm

    Glad you enjoyed it V 🙂


  8. Anonymous
    November 24th, 2013
    7:36 am

    From a girl’s perspective: don’t use really cheesy pick up lines, don’t bullshit to her about how she’s special/different from other girls if you dont mean it (a lot of girls can spot a lie these days), and don’t try too hard. Just be yourself – be polite, be upfront and honest, and be respectful. Smile and genuinely listen to her. Don’t pull any moves too fast. Call her when you say you will… etc… I know a lot of guys have this opinion that “nice guys finish last” but its not true. I only go for nice/good guys. Most girls would prefer the nice guy for longer relationships and they usually have much nicer things to say about the nice/good guys. I think eventually people tire of bad boys and every player’s reputation slowly spreads, which is unappealing.


  9. Anonymous
    November 24th, 2013
    7:40 am

    Also from a girl’s point of view, the biggest turn offs in a guy are: arrogance, cockiness, or when he talks about how much of a ‘scoring’ player he is. Being shallow and having a big ego is also unattractive. Honesty and respect are much more appealing in any person.


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