A lot has been written about the first date. How to dress, how to act, how to pretend that you’re a decent guy. The truth? That’s the easy part. On the first and second dates, you’re still coasting on the initial rush of attraction, the exchange of backstory, the spark of the unknown. Date Three brings something else entirely: reality. And there are many ways to botch it.
Blunder 1: You Serve a Liquid Meal
Getting drinks as your first date is a hard strategy to beat. Neither party is locked into the rigid structure of a sit-down dinner, so, happily, either one of you can bail at your convenience (and you can save a nice chunk of change.)
As a second date, drinks are still acceptable, providing you mix up the venue and show a bit of range.
As a third date, drinks suggest three things: 1) you are cheap; 2) you are boring; 3) you are an alcoholic. By the third date, you should be eating dinner together.
Blunder 2: You Forget Her Stories
The early glow of flirting, kissing, and sexual tension can be a deodorant, of sorts, that covers up a nasty odor: you don’t listen. If, on the first date, she told you charming anecdotes about her job as an indie-theater director, you disqualify yourself by later asking, “So what do you do?”
Ask lots of questions and remember the specific details. And if you don’t care about her indie-theater job or any of her anecdotes, well, this is the time to cut bait. (Before hooking up, not after. You are not a monk, but you are not a douche, either. For more of that, find out your dating douchebag score here)
Blunder 3: You Go Dutch
There is indeed a time in every relationship when couples begin to swap the tab, take turns, buy each other rounds. That time is not now. Even if the girl offers to pay, the third date is too soon for Dutch.
Now, to clarify: if you buy her dinner, it’s perfectly acceptable (and appreciated) for her to pick up a round of drinks later in the evening. But if you let her pick up dinner, it’s perfectly acceptable (if unappreciated) for her to pick up a new guy later in the evening.
Blunder 4: You Relax Your Manners
We’re all on our best behavior early on. We’re polite, we’re not yakking away on the phone, we’re not yawning. It’s only human nature that, over time, this politeness will ebb. Over time. Not on the third date.
One of the worst offenses is bad Text Etiquette. It’s too early to start texting your buddies while you’re having dinner, or checking your phone for fantasy football stats, or pounding out emails. Save your true, sloppy self for when it matters–marriage.
Blunder 5: Your Conversation Can’t Find a Higher Gear
Back in the glory days of Bill Walsh and the 49ers West Coast Offense, the coach would script the first 15 plays of every game. This gave the offense confidence. Sharpness. An edge against the defense.
Once that template was used up, the team needed to react to the defense, make adjustments, find the groove of the game. Dates One and Two are those first 15 plays (for both of you): where you’re from, where you work, the nuts and bolts of human exposition. The third date? It goes off-script. Now is the time for more organic, more substantive conversation, and you have to step up if you want to keep seeing this woman.
Blunder 6: You Smother Her
You are not yet her boyfriend. So between Dates One and Two, your worst(ish) mistake would be daily phone calls 
, an onslaught of texts, the presumption of intimacy. Too much, too soon. Of course, the pendulum can’t swing too far. If you ignore her completely between dates, she’ll assume you’re aloof and only want sex. Which may or may not be true.
Blunder 7: You Meet the Friends
There is a theory that argues the following: the best indicator of a person’s character is the company they keep, so, logically, you should meet your date’s friends as soon as possible as a “litmus test.” If the friends suck, so will she (Obviously, the same applies for you and your friends.)
The theory is too clever by half. While true in spirit, it’s still too much, too soon. This isn’t a hard and fast rule, of course–group dates can and will be fun–but you owe it to yourself to first create an incubator, to see if you have real chemistry, to keep growing your connection before trotting it out in public.
Plus, there’s the very real concern of physical awkwardness–do you hold hands, kiss, split off from the group midway? No reason to inject more anxiety into a still-fragile situation.
Blunder 8: You Over-Share
The canned stories are used up, she knows where you went to school, the playbook has run its course. This does not give you license to plunge deep into your soul and uncork your darkest, most personal stories. She is your date. She is not your shrink.
Blunder 9: You Wuss Out
If you conclude the third date without kissing her, congratulations, you’ve just done something very special: you’ve made a new friend.
True, you should never be creepy or smarmy, but by the third date, there’s no excuse for shyly walking away after you hug her goodnight, patting her on the back like she’s your sister. She may very well be waiting for you to make a move. Take a chance.
Blunder 10: You Presume to Collect Your Reward
Careful. This is where guys can get greedy. This is where guys make a critical fallacy: they assume that the “Three Date Rule”–which some girls follow–means that, as a “rule,” every girl is ready to hop into bed on the third date.
The fact that you have entertained her on three separate occasions does not, by default, give you open access to her vagina. True, she may wave you in, but don’t make the assumption until she does.