11 Mistakes that Ruin First Dates (and How NOT to Make Them)

I’ve been on innumerable first dates over the years. And I’ve coached all sorts of students through limitless more dates. And if there’s one thing you find out, it’s that the first date is absolutely, inescapably crucial to how things play out the rest of the courtship.

The first date is a make-or-break event. Hit a homer on the date, and the rest is pretty magical.

A great first date makes your date partner comply more with you (she does what you ask of her). It causes her to cut you more slack (i.e., she’ll let you get away with more). And it piques her interest in you (now she wants where things go with her and you!).

But there’s plenty of opportunity to botch the first date, too. And a lot of folks do, a lot of the time. There’s all this uncertainty: you don’t know your date well yet (certainly not as well as you’ll know her later on... if all goes well). You don’t know what she likes, what she’ll respond to... what ‘does it’ for her. You might think you do – but you don’t. Not yet.

Even if you’ve known her a while, well... people have their ‘social selves’, which is what they present to their friends and acquaintances. Getting her on a date is about getting past this social self (and finding out whom she really is).

On top of it all, you may not be all that sure what to do with your date, what to discuss, or where to take her. So in addition to all the question marks of your date herself, there is also the question mark of the date.

And the more question marks there are, the rougher things get.

In this article we’ll look at 11 of the most fatal mistakes you can make on first dates.

But don’t worry – we’ll also talk about how to avoid those mistakes, to make your first dates go as smooth as butter (and make your date melt like butter while she’s out with you, too).

Good date planning is pivotal. It’s your homework before the big event. Fail to date plan (i.e., ‘winging it’) is like when you show up for a mid-term exam without having studied. Or like when you make a career-defining presentation to the board, which you decide not to prepare for in advance to instead ‘play it by ear’.

You might get lucky. It’s a lot more likely though you’ll just strike out.

Now, you won’t need to do a lot of homework. You don’t want to obsess about any one date SO MUCH that you psyche yourself out.

So the plan is to map out a few important details. Then, shelve the date (mentally) until it’s go-time.

In this section, I’ll lay out four of the most important pieces of the date plan for you (and how to not get them wrong).

Our four (4) major date planning mistakes are...

Have No Plan for the Date

It all comes back to this.

If you don’t have a plan, you are just ‘winging it’. Winging it works fine if you are already very experienced and know exactly what you will do. Or if your date is the one in charge, and you are just along for the ride.

However, if you are not very experienced, and if you are the one expected to lead the date (and if you’re a guy, you are the one expected to lead the date), you need some preparation.

What prep do you need? You need to know:

• Where you will take your date (check out my article on date templates)

• What you will do with her at these places you take her

• How long you will spend at various places

• How you will transition between places, and what you will do at the end

You should spend about 30 to 60 minutes on date planning, especially when you’re new to dating. Even when you’re experienced, you will almost certainly notice a big difference in how dates you plan vs. dates you don’t turn out. It might feel like ‘homework’, but it helps – a lot.

Don’t build a complicated plan. Just a basic skeleton to follow, so you don’t have to think while you’re on the date (and, instead, can just enjoy being with your date).

The point of the plan is to get the mental heavy lifting out of the way before the date – to let you have as fun, free, and fruitful a first date as you can.

Pick an Inconvenient Time

In your rush (or excitement) to schedule a time with your date, it’s all to easy to make a BIG first date mistake: you choose a time for the date when she, or you, or both of you, ends up squeezed on one or both ends of the date.

I used to do this all the time as a novice dater. The absolute worst date for me timing-wise was one I picked where I was squeezed at the start and the girl I had a date with was squeezed at the end. I ended up running about 40 minutes late, we had a very short date, and then she had to leave because of an appointment she had. I never saw the girl again... and didn’t particularly enjoy the date (quite a bit of rushing to get there. Followed by not much payoff for the trouble).

It can be tempting to settle for the first time someone pitches when you discuss when to plan the date for. But don’t do it. Check your schedule and her schedule first to make sure you’re not squeezed on either end.

The first date goes much, much better when neither of you has to rush to get there, and neither of you has to rush to leave.

Here’s an easy way to check for time: when you text a girl to set up a date, ask her her schedule first. When she comes back with it, if the window sounds at all tight, ask for a different time. Like so:

You: blah blah we should grab that bite this week. What’s your schedule like?

Her: I have some time on Thursday I think.

You: Hmm. Sounds squeezed. If we’ll be rushing to fit each other in, maybe another time’s better? Got a more relaxed time we could meet?

Her: I could probably do Saturday!

You: Cool. Any time on Saturday is good?

Her: Yeah, I have most of the day open!

And just like that, you’ve got a full day to work with... instead of a tiny, compressed window. Fatal first date mistake = avoided.

Choose a Non-Intimate Location

It’s pretty common to pick FUN spots to hold dates. You know... amusement parks, parties, roller rinks, karaoke night at the local dive, a trip to the 12-screen multiplex, a night out dancing at the club. These can indeed, sometimes, work great. But... there is a ‘but’.

The ‘but’, of course, is that fun is not enough to cause a girl to end up with you in and of itself. Fun works as a wonderful supplement to your own personal offering on the date... but for her to get together with you (or want to meet up with you again), you must build that personal connection with her. And that is tough to do in non-intimate places.

It can be fine to start your first date out in a non-intimate date location. Yet at some point – hopefully soon into the date – you are going to want to move your date somewhere more intimate.

Here are a few intimate date locations to get your mental gears turning:

• Cool cafés
• Ice cream parlors
  
• Laid back lounges
• Low traffic / darkly lit dive bars
• Small/unfrequented stretches of beach or park
• Informal restaurants / sandwich shops
  
• Your place or her place
  

Once you’re one-on-one with her in an intimate environment (without others looking on or noise and chaos distracting her), it’s time to work your dating magic. (you can find tons of step-by-step specifics on everything to do on the actual date itself in my new flagship course One Date. One Date gives you the tools and process you need to take her as a lover or girlfriend in just one simple, easy-to-get date... and have loads of fun doing it)

Forget to Bring a Story or Two

One of the things that always sucked for me when I wasn’t as experienced with the opposite sex was those situations where you meet up, and nobody knows what to say. You ask her “So... what’ve you been up to?”

And she says not much. And asks you so... what’ve you been up to?

Oh. You haven’t been up to much either. Things start to feel stale real quick.

There’s an easy-as-pie way to solve this though: keep a few stories at the ready in your back pocket. These should be recent stories... you don’t want to kick off the date with “Oh hey, let me tell you about this crazy thing that happened to me last year.” It feels... not that relevant.

Instead, what you want is recent. Fresh. Your stories don’t have to be awesome or exceptional. They just have to be mildly interesting, and seem current.

For instance, you might tell her about how you got stuck in gridlock today and realized it’s the perfect time to meditate... just turn off the radio, clear your thoughts, and get your mind right. Or you might tell her you hit the gym today and there was this fat guy there again, and that he is one of the only people you consistently see at the gym. And mention that he might be out-of-shape now, but you’re really starting to root for this guy, just purely because of how much grit he’s got.

Little things like this. Current, kind of interesting – that’s all it takes. Before your date, think up a few stories like this you can relate if it’s slow going to get the conversation started once you’re on the date, and slide those tales into your back pocket to pull back out as needed.

Even if you’ve got your date planning nailed down good and tight, you can still slip up on the date itself. There’s margin for error on your dates (you don’t have to be perfect). However, the following three first date mistakes you can make on the date with a girl can be ruinous for your shot with her. So you’ll want to not make them.

Make Things Too Serious

When you like your date a lot, it’s easy to put pressure on yourself.

A lot of pressure, sometimes. When you do this, it’s also easy to forget to make the date enjoyable.

An over-serious date is not a fun date. No one wants to show up for a date with someone else, only to get slathered with that someone else’s nervous energy, pressure, and expectation. You don’t have to be (and shouldn’t be) a clown. However, you do very much want to be playful on dates.

The worst dates you’ll ever have will be the ones where no matter what you do, the date has all the levity of a funeral procession. That leaden, wooden, stifling feeling of no-fun... it’ll make your dates go toes up.

So be playful. Flirt. Tease her. Have fun with her. Make it a good time – for you both.

Sit or Stand Too Far Away

Proximity is huge. It makes the difference between your date feeling like you and her are two peas in a pod... or you and her are two peas in separate pods, far apart from each other, communicating via smoke signal or carrier pigeon (“How’s the weather over there? Much rain or wind?”).

Don’t make the first date mistake of letting your date position herself too far away from you... or positioning yourself far away from her yourself. People sometimes do this because they’re unsure what is the ‘proper’ thing to do – or they are trying to be polite. “I don’t want to sit too close to him,” she thinks. “It might look needy or impolite.” Well, if you let her do that, she’ll certainly look polite... but you will both feel awkward for the entire rest of the date. It’s unlikely the date’ll recover after that (sometimes you can salvage it... but poor proximity packs a wallop).

Do not worry about being polite. Instead, be close. Politeness is for strangers. And you don’t want to be strangers with her, right? Kind of defeats the point of a date.

If your date is the one who sits or stands too far away from you, get her out of the polite zone and closer to you with an invite: “Come closer, you’re so far away!” (better to have her move closer to you, than you to go to her... especially if she was the one who set herself up far away from you. Make her come to you; don’t chase her)

Don’t Get Enough Touch In

A few weeks ago we talked about the no-touch technique. With this approach, you go long periods – perhaps as long as an entire date – without touch. It’s a great technique, but it’s only for advanced daters... and even then, most advanced daters won’t go the whole time without touch.

The average dater needs to touch. Touch is an incredibly powerful means of communication. And it communicates things to her and about you it’s next to impossible to convey without touch. Even if you get her to keep close proximity with you, if you do not touch, it’ll be very hard to move your date past a certain point. A first date without touch is, quite often, a date that won’t end well (or lead to anything beyond that first date).

So, make sure you touch. If you need some help to figure out how to touch a girl or where to touch her, make sure you give my article on touch a read-through:

• 7 Ways to Touch a Girl + 3 Ways to Have HER Touch YOU
  

“The end is important in all things.” So says the Hagakure, the Book of the Samurai. The full quote is quite beautiful: “In the Kamigata area they have a sort of tiered lunch box they use for a single day when flower viewing. Upon returning, they throw them away, trampling them underfoot. As might be expected, this is one of my recollections of the capital (Kyoto). The end is important in all things.” The end is important with lunch boxes, and it is important in dates as well. A date that ends well is one that leads to wonderful things; a date that does not end well is one that likely leads to nothing more.

Two of our ‘end date mistakes’ revolve around date planning again. However, I did not include them in the earlier section on planning, because 1.) they are about the end of the date, not the beginning, and fit better in the section on date ends, and 2.) they require a certain degree of planning on-date as well; you will not always be able to map everything out in advance.

So let’s discuss our last set of four romance-rending first date mistakes you can make... and talk how to not make them.

Fail to Contingency Plan

A contingency plan is simply “If X goes wrong, I can Y instead.” Like:

• If I ask her to change venues after we’ve been at the café a while and she declines, I can wait five minutes, seed a different venue change, and another five minutes later propose that change.

• If we arrive at the bar we’ll head to for the second part of our date but it turns out to be too crowded, there’s a neat little lounge three blocks down we can head to instead.

• If it turns out we have nothing in common and can find no common ground but I still want the date to move forward, there’s a super fun miniature golf course nearby we can bounce to to have a good time at where it’ll be a cinch for me to have a lighthearted teasing/flirting/fun date with her instead of a deep connection date.
  

Those are contingency plans. Without contingency plans, you may end up in difficult situations with no way out. You won’t always be able to think up a solution on the fly. Ever have a date with a girl where you propose something, and she declines it, but you’d planned nothing else? Then you drop into “Oh man, what do I do now” mode, stress out, and the date ends a bit later and you never see her again? That’s an example of a missing contingency plan that sinks your romantic hopes with your date.

You’ll tend to form a bunch of contingency plans naturally over time as you date more and encounter more unexpected dating scenarios (and have to figure out how to deal with them). However, you will want to plan for any you think you’re likely to encounter on the date in advance, and you’ll want to plan for any you foresee as possible once you’re on the date, whenever you have a few moments to think.

If, for example, it doesn’t feel like you and her have much in common (as will sometimes happen with girls you get dates with), plan your contingency for that ahead of time. Usually that will mean some alternate fun/mindless thing you can do together you will both enjoy... and that builds a commonality in and of itself (i.e., you and her both enjoy this fun thing you do together). If you know the place you’re headed to sometimes gets very busy, plan a backup venue you can go to instead. Or if you’re not sure the place’ll be open, ditto.

On the date itself, you’ll sometimes run into situations that behoove you to cook up a backup plan on the fly. Anything impulsive you and her decide to do usually fits this bill. For instance, if she says “Hey, I know this great little spot we can head to!” and you say let’s go, as you walk with her, you need to start to contingency plan for what happens if you get there and the spot is closed or no good. I’ve noticed over the years that women have a strange tendency to propose places that often end up being closed when you get there... who knows why. If you failed to plan ahead for this, when you get there and she becomes bummed out, the date’s over. If you contingency planned, however, then when you get there and it’s closed, you can immediately reroute the energy into “You know what, there’s another neat place nearby with these super comfortable booths and the most amazing late-night pancakes. We should head over there.” You’ll keep her energy up, keep the date alive, and most likely save things from what might otherwise have been an unfortunate end.

Fail to ‘Awesome Plan’

If a contingency plan is a ‘things are worse than expected’ plan, there’s still another way you can accidentally blow up your dates – and that’s by failing to ‘awesome plan’. By ‘awesome plan’, all I mean is “What do you do if the date goes far better than you expected?” (technically, this is also a contingency – but since contingency usually means something negative in the vernacular, I’ve split them up).

As you know if you’re a regular Girls Chase reader, attraction has an expiration date. And if you miss an escalation window – and you fail to capitalize on one of those moments where your date is so excited, because things are going so well – expired attraction is very often what you’ll end up with.

Ironically, things can go so well the date collapses... if you didn’t have a plan in place to deal with things going so well.

A lot of my first dates went this way when I was new to dating. I’d go out thinking, “Okay. I’m just going to talk with this girl, flirt with her, and get comfortable with her. And then at the end of the night we’ll end the date.” Instead, I’d do better on the date than I’d anticipated, my date would get all excited, but I’d freeze up and not know what to do with her. So instead, I’d stick with the plan, eventually end the date, and then I’d... usually never see the girl again. The date went far better than anticipated, and when I failed to lead it to the awesome places it was headed, my dates got annoyed or disappointed. And once they were annoyed or disappointed, they didn’t want to see me again after (and experience more annoyance or disappointment).

You always want to have an ‘awesome plan’ in hand for if things go better than you expect. You won’t be able to perfectly predict how a date is going to go. Some dates you think will be great yet turn out to be chores. Other dates you don’t expect much from, yet they go awesome.

It’s those latter dates we need an ‘awesome plan’ in place for... lest you end up like I used to back in the day.

An awesome plan can be as simple as “If this girl starts to show signs she’s very into me, I’ll just invite her back home to drink and relax.” Or if you’ve planned a quick get-to-know-you style date, sometimes you’ll show up for these and you and the girl hit it off more than expected. In that case, you won’t want to stick to the quick format; you’ll want to add more to the date, and continue to spend time with her. If you like to spend time with her, and she likes to spend time with you, why not continue to spend more time with each other? With an awesome plan in-hand, you can.

You’ll also want to remember to awesome plan on-the-fly when you start to see better signs from a date than you expected to see. You can’t plan every situation out in advance; a lot of it requires you to evaluate and adjust on the ground. If you get out on a date, and things start to pick up and the energy begins to build and she flirts more or gets closer to you or puts other great signs out there, start to think about how you want to move the date along to help it reach the higher heights it’s headed to, faster and more reliably.

Don’t Respond to Her Signals

The sister error to ‘failure to awesome plan’ in our ‘ruinous first date mistakes’ list is the failure to respond to your date’s signals. Those signals come in all shapes and sizes, but all boil down to the three categories Alek discussed in his article of two days ago:

• Proceed (green light)
• Stay where you are (yellow light)
• Back off (red light)
  

Planning is excellent. You should absolutely do it. However, a date is a meeting between two individuals. And there’s a lot there you cannot plan. You must be able to stay responsive to the signals your date sends you.

If you tease her a little too much for her tastes and she shows discomfort, back off and repair the connection: “Hey, I’m just kidding. You’re an awesome person. I really dig your blah blah [something you like about her].”

Or, on the other hand, if you talk with her for a while and she starts to signal boredom, find a way to mix a bit more challenge into the date. If you pick up a copy of my One Date course that’s about to come out, I give you a bunch of ways to keep the interest level (and challenge level) on your dates at a simmer. You don’t want it too hot (to the point it boils over and you need to back off a bunch); you just want it on that steady simmer where she is challenged enough to have fun, and doesn’t slip into boredom. The second part of the date-acing formula I give you in One Date is completely about this.

It’s not hard to keep an eye on your date and stay responsive to her. You’ve just got to remember to do it... especially when you’re new. There’s a lot to keep track of (though less so if you planned well – like we discussed in Part 1 of this article!), but watching for and adjusting/responding to the signals she gives you is one of the foremost things for you to focus on on your dates, if you want to avoid the bad date trap and instead make your dates as exceptional as possible.

Don’t End the Date Well

Back to that “end is important in all things” bit. How you end the date determines, to large extent, your future with the girl you take out on that date.

If you don’t end the date well, no matter how well you did on the rest of the date, there’s a good chance your efforts were for naught. You may sometimes recover from a botched ending... but you can’t count on it. Very often, the ending is the thing that sticks in the mind the most.

You have different ways to end dates well. If you’ll take her to bed this date, that is, of course, the ideal, and one of the more satisfying (and often romantic) ways to cap off a date. If you won’t take her to bed, however, so long as you end the date on your terms, without cresting her emotions too high (and leaving her unsatisfied), or leaving on a down note, you’ll be in good shape.

The emotions you end the date on are key. Don’t get her too excited and fail to deliver. If you get her too excited, you will simply have to take her to bed on this date... even if you hadn’t intended to. Or you may be able to release some of that tension with a date-ending kiss (a kiss you should also end yourself; don’t make her end the kiss first – it’s far better for you to end it).

By the same coin, also be careful not to end things on a down note. If the date’s dropped off in energy a bit, bring it back up before you draw things to a close. Elsewise, what she’ll remember best is that toward the end, she wasn’t having fun anymore. And then it ended. Bring her up before you cap off the date.

So long as you end your date with her with grace and intrigue, she will want to see you again.

A good first date is lots of fun to run, and can be a wonderful experience for you and your date both. There are also plenty of ways to mess up... however, with a little forethought, and some awareness on the date itself, you can clear these hurdles.

One parting thought: keep in mind that your date should feel challenged only when you want her to feel challenged, and fun/free/at ease the rest of the time. So long as you can maintain that cadence – where she is challenged when you want her challenged and free/fun/at ease the rest of the time – you’ll deliver one great date after another to every girl you take out.

I hope this article’s given you some ammunition to make your dates a smoother, more pleasant experience for both yourself and the women in your life.

And if you don’t have too full a dance card right now, well – now you know how to deliver up an awe-inspiring romantic performance. I expect you can parlay that fresh knowledge into a fresh bump in confidence, and ask out a few new girls to help fill that dating pipeline.

Be well, and happy dating.

Yours,

Chase Amante