How To Get A Second Date (By Acing The First)

First dates can be stressful. You’re trying to find the right balance of “impressive” but “non-chalant”. You’re stressing where to take her, what to say, who’s going to pay for what and – most of all – do you go for the kiss at the end of the night? Then, of course, if everything goes well, is there going to be a second date or are you going to be waiting by the phone that never rings, desperately trying to summon up your latent telepathy and trying to implant the idea of calling you back through thought projection?

"Hey, it's me. Again. Just checking to see if you're alive. ANd, y'know. Want to see a movie this weekend. Or some weekend. Or something. Call me?"

“Hey, it’s me. Again. Just checking to see if you’re alive. And, y’know. Want to see a movie this weekend. Or some weekend. Or something. Call me?”

Fortunately, it’s all pretty simple, as long as you keep your head. If you want to get that second date, you need to know how to ace the first date and what common pitfalls and mistakes you need to avoid.

A Great First Date is NOT An Interview

A great first date really isn’t that complicated.  You want to focus on three things: fun, conversation and a hint of sexual tension. You want your date to go home thinking about what a great guy she just hung out with and how much fun it would be to see him again. This is why most of my favorite first dates are structured to avoid the “audition” frame that so many first dates turn in to – sitting awkwardly across from each other, asking the 10 standard getting-to-know-you questions everybody asks and spending most of the date inside your own head instead of, y’know, enjoying yourselves.

This is one of the reasons I prefer to avoid the coffee date and the dinner-and-a-movie date: they’re cliche and boring and minimize any real chance for interaction. My only real exception to this rule is for online dating; a low-investment date like coffee is more about a gut check than an actual date. You’re checking how you feel about one another when you meet in the flesh… not to mention doing basic due diligence, trying to make sure that one or the other isn’t a psycho axe-murdering cannibal. Even so: a coffee date can be made more than just strangers asking questions while trying to pretend that the Starbucks they’re drinking doesn’t taste like burned ass. Pick a coffeehouse that does more than just coffee. Some double as music venues – some in Austin even have improv and stand up comedy performances. Many others have board games, which can be a great ice breaker and allow for that competitive aspect that can get your juices flowing and the flirty trash-talking sparking.

An important, yet often neglected key to avoiding the awkward “interview” vibe on a first date is positioning. Think of your average job interview: you’re staring nervously at your prospective employer who sits behind their massive desk as she asks the questions that decide your fate.

Now think about how you position yourself on a first date: sitting awkwardly across from one another from across a table while you ask questions and hope you don’t screw up. A simple change of where you’re sitting – from directly across to perpendicular – completely changes the tone of the interaction.

Of course, you might have had way cooler interviews than I have...

Of course, you might have had way cooler interviews than I have…

By sitting next to your date or at an angle, you remove the feeling that you’re at odds with one another or the impression of a barrier between the two of you. It feels much friendlier and less confrontational, which will put the both of you at ease. It also – critically – makes it easier to engage in casual physical contact that would be awkward to attempt sitting directly across.

Your Date Is About The Two Of You.

I spend a fair amount of time out and about and eavesdropping on dates is a guilty pleasure of mine… which is why I’m continually astonished by the number of people who make this very basic mistake: they don’t give their dates their full attention.

You would be surprised just how many people do not understand that when you’re on a date, it is about the two of you, period. Unfortunately we live in a world full of distractions and constant interruptions that can be hard to tune out – especially if you’re used to being wed to Twitter, Facebook or your email. Your date is about getting to know each other, not getting to know her AND checking up on your Facebook friends or the massive elbow strike that St. Pierre just landed on Diaz’ jaw. 

Which brings me to my point: turn off your motherfucking phone.

You wouldn’t think that this needs to be said1, but far too many people blow a perfectly good first date by not cutting their electronic umbilical cord. I have personally seen far too many people on dates lose track of their conversation with their dates because they put their iPhones on the table and keep glancing at them every time a new email or text chimes in. It’s annoying and it’s profoundly disrespectful to your date – you’re explicitly telling her that she is not nearly as interesting as the latest update to your fantasy football league or whatever @PartyInMyPants69 had to say about your latest retweet. If you can’t go more than 30 seconds without checking your phone, switch it off entirely. If you have some reason you absolutely must be reachable – a family member’s medical emergency is acceptable… barely – then set a filter; most smartphones have a “Do Not Disturb” function that will only allow certain numbers to ring through. 

The message he's missing says "U r not getting any 2nite".

The message says “U r not getting any 2nite”.

Other distractions can also ruin the flow of your date. Many bars – and some restaurants – have TVs; it can be hard to ignore these when they’re constantly flickering in the corner of your eye. The obvious answer is to avoid dates at venues with TVs or projectors. However, if you find yourself at a place with televisions, turn yourself away from them. Get them completely out of your field of vision – I have seen far too many people get caught up on the TV behind their date rather than on the person sitting directly across from them.

Believe me: your date will notice that you’re distracted. And she will not appreciate it… which means that not only are you not getting a good-night kiss, you’re going to be lucky if she doesn’t suddenly have a fake emergency that needs to be taken care of right away.

Conversation Is Key

Want to know one of the signs that your first date is going well? Neither of you wants to leave because you’re having such a great conversation. There’s nothing quite as appealing as someone who can intrigue your mind as well as your squishy bits… and a bad conversationalist can kill any sexual interest deader than Christian Slater’s career.

You don’t need your own personal Cyrano DeBergerac2 whispering poetry in your ear to master conversation, you just need to follow some simple rules.

Ask Good Questions:

There’s nothing worse than a date who will only talk about his favorite subject… especially when that subject is him. A date is about the two of you, which is why you want to make sure that you’re showing interest in your date… and the best way you can do this is by asking questions. Questions are part of how we find commonalities and build rapport with one another… and they’re how you keep from running into those awkward silences that leave you both feeling uncomfortable and scrambling to talk about anything.

Just don’t be boring… those standard 10 First Date questions will get you nowhere. Instead, ask your date about her hobbies, her passions, the things the craziest thing she’s ever done or what she would do if she had no chance of failure. If you need to get a conversation started, I always like to ask “Who was your favorite Bond girl?” or “Who was your favorite of the Doctor’s companions?”

(Hint: the correct answer is either Martha Jones or Donna Noble. Just sayin’)

Tell Stories:

When it’s your turn to share about yourself, you want to have some stories to tell – that crazy night you and your friends crashed a VFW dance dressed in vintage fashions and learned how to swing with WWII vets3 , the epic road trip you took with your friends or even just the wacky things that happen on a daily basis. I go into what makes a good story elsewhere, but the basics are simple: you want to keep them relatively short, vivid and should have an ending that provokes a “awww”, “cool!” or a laugh.  These stories are chance to subtly brag about yourself and let your date know what a relationship with you might be like… so you want to paint as attractive a picture as possible.

(Obviously, if you don’t have stories to tell… well, really, you need to go out and start collecting them!)

Avoid Negativity

Negativity has no place on a date, especially a first date. Negativity is the black hole from which attraction and fun cannot escape. This means no bitching or complaining about your job, your friends, your life, the restaurant or anything else. Your job may well suck… so don’t talk about it. Just say “yeah, it’s just something to pay the bills for now” and change the subject. Complaining about your friends will just make your date wonder why the hell they’re in your life in the first place.

This goes doubly so for your exes. I don’t necessarily subscribe to the “no talking about your exes” rule, but you definitely do not want to talk shit about them. All complaining about an ex does is tell your date how you’re going to talk about him if/when the two of you don’t work out… and the last thing you need to do is plant that idea in his head.

Most importantly though, it’s hard to have fun when the other person is relentlessly negative – and fun should be your goal. If you have nothing positive to say about a particular topic, change the subject and move on.

Dial Back The Booze

First dates and alcohol go together like Japanese school-girls and giant mechs – they seem like a natural fit, but the potential for trouble often outweighs the benefits. It’s natural to want to have a drink or two on a date – a shot or two of Irish courage to ease those jittery nerves, another to act as a social lubricant, yet another because you’re pretty sure the first two got lost on the way to your stomach and you need to send out a search party – but it’s entirely too easy to lose track and end up with problems you could have otherwise avoided. The line between a pleasant buzz and “removing a much-needed mental filter” is thin indeed, and you don’t want to end up tripping over your own dick because the whiskey loosened your tongue a little too much.

Similarly, if you’re not careful, you can give the impression that you’re trying to get your date a little drunk, which will send up the “creeper” vibe faster than just about anything else you can do, even if your intentions are perfectly honorable.

This isn’t to say that you should avoid alcohol entirely – just keep it to one or two before switching to water or soda.

Relax

Look: we all know that first dates can be tense, nerve-wracking affairs, but you need to relax. Remember: the key to a great first date is to have fun… and if you’re so caught up with anxiety and stress that you could vibrate through space and time, that’s just not going to happen.

"Here she comes. Remember: don't throw up. Don't throw up, don't... ::urk::"

“Here she comes. Remember: don’t throw up. Don’t throw up, don’t… ::urk::”

Part of the reason for these nerves is the self-imposed pressure to make a good impression. Some people get so concerned with the idea of impressing their date (and upping their “value”) that they end up going much further than they need to – expensive dinners, hard-to-get tickets to shows, large bouquets of flowers… it’s nice if you can afford it, but sometimes not only is it a case of diminishing returns but sometimes you end up with the opposite effect and scare your date off. Frankly, less is often more; a fun night of bowling and a couple Miller Lights is going to go better than an uncomfortable dinner at a gourmet restaurant with a bottle of Veuvet Clicquot.

But just as important as not trying to go over the top to impress your date is to not put so much pressure on yourself that you can’t actually enjoy yourself. If you’re so keyed up about making everything go perfectly, you’re going to end up a twitchy bundle of nerves… and that’s going to make your date uncomfortable too. Frankly, the best attitude you can adopt is one of “No big deal”. Dating disasters – spilled drinks, inconvenient stains, spoiled plans – suck, but being able to handle them with aplomb, grace and a sense of humor will not only get you past them but will actually make your date that much more memorable and charming. Being able to take a mistake in stride and good cheer makes it much easier to recover, and that recovery will say more for you and your sense of confidence than anything else you do… and that will impress your date.

Even in the worst moments of awkwardness, be willing to face it head on. Nothing kills the awkward faster than calling it out. Acknowledging that yes, things might be a little uncomfortable or that you’re a touch nervous isn’t a sign of weakness, it’s a sign of strength – you’re confident enough to be honest with your date instead of trying to put up a false front. Plus, it’s almost guaranteed that she’s feeling just as nervous as you are; being the one to call it out will make her feel better and help release all that pressure.

 

Getting That Next Date

At the end of the date, there are usually two questions remaining. The first, of course is: “when should you call?”

While I understand the worry about not appearing needy, I’m of the opinion that if the two of you were having a great time… why wouldn’t you want the conversation to continue? Hell, if the two of you hit it off, chat the night away as soon as you get home.

As a rule of thumb, however, I recommend a text some time after noon on the next day. Let your date know what an awesome time you had and that you want to see them again. Be clear on your interest; you don’t do yourself any favors by trying to pretend that you’re too cool to care. It’s not expressing interest that makes a person appear needy, it’s the manner in which he or she does it. It’s one thing to say “I’d like to see you again,” and quite another to say “Please please please go out with me again” five or six times into their voicemail.

Which leads nicely into the other question: “How do you get that next date?”

Ideally, the two of you have had such a good time that you’ve already talked about going out again. However, that doesn’t always happen… so it becomes incumbent upon you to set up the potential for another date. One thing that I have had success with is seeding the idea of the next date during the first. At some point, you will find the opportunity to plant the idea of a future date – usually when you’re talking about your passions. I would mention some upcoming event that I was looking forward to: a band playing in town, a gallery opening, a street-fair… something fun that would be occurring in the near future. I would talk it up a little… then let it drop and move on to another topic. Towards the end of the night – or in the conversation the day after – I would bring it up again; “Hey, listen, I’m having a great time with you, and I’d like to see you again. I’m going to $FUN_THING next week, and it’d be great if you came too, I think you’d really enjoy it.” It’s relatively low-pressure and doesn’t feel like it had been dropped out of the blue – you have some pretext for bringing it up. It also establishes that A) you have a life, B) that you’re not waiting with sandwiches by the phone for her to call you back and C) that fun event would be even more fun if he or she were there.

Go For The Kiss

Notice that I said there were only two questions? That’s because as far as I’m concerned, you should always go for the good night kiss.

Now to be fair, whether to kiss on the first date or not is often a matter of contentious debate and personal preference. Some people resolutely won’t while others have no problem burning up the sheets if the date goes well enough.

Personally, I’m a fan of kissing before the end of the date, but that’s me; if you’re not confident in your ability to read the signs that she wants you to kiss her then it’s not going to hurt if you wait until the end of the evening. I am of the firm opinion that, absent a clear wave-off, it’s worth at least making the attempt… provided you’re classy about it. If you don’t – especially if you haven’t been 100% clear from the beginning that the two of you are on a date – you run the risk of being too timid and possibly inadvertently signaling that you’re not interested in your date. So as you walk your date back to the car or to their door, pause. Tell her what a good time you had that night… then lean in slowly. Give her the option of giving you the cheek – or even a complete wave-off – if that’s what she wants. When you do kiss her, keep it light – which means no tongue – and just the once. If she wants you to kiss her again, she’ll almost certainly let you know in no uncertain terms. Let your date take the lead in how intense to go – better to hold back a little than to inadvertently maul them instead.

If you do get the cheek, then you act as though that’s exactly what you intended to do. Don’t call attention to it – that doesn’t help. Accept that she’s not ready to kiss you this time and you will have far better odds of there being a next time. Acting like a cock about it or trying for the kiss anyway is only going to guarantee that there will be no second date.

Ever.

  1. Although in the spirit of full disclosure, I will freely admit to this being something I’m especially bad about []
  2. although don’t think I haven’t been planning an app with that idea in mind []
  3. which I’ve actually done []