How To Properly Alienate A Woman On The First Date

by Scott Spinelli

I've been on a number of first dates in my life. Second dates, third dates, bad dates, good dates, meet-up-at-the-bar-and-buy-one-drink-before-we-have-sex-so-you-don't-feel-cheap dates. I've pretty much run the gamut in my 25-years and counting, and I have to say, that's pretty impressive considering I started dating fairly late into what would be considered my sexual prime (which, for those counting, has already ended if my current success rate is any indicator).

With all my experience considered, I'm pretty confident with regards to knowing how to act if you're looking to impress a woman. Honest admission time: I am a single man, no girlfriend to my name or Facebook account. I can hear you, reader, wondering how it is I can claim to be so all-knowing, yet not have any actual current success to prove it.

Well, to you I say, just because you know how to do something doesn't mean you can actually do it.  I know how to dunk a basketball (I believe it involves some combination of jumping, palming a basketball, and ramming it through the hoop with loud grunting noises optional), but I can't actually touch the backboard.

However, it isn't much fun to talk about impressing a woman on a first date, now is it? No, I prefer the rarer topic of alienation. If your mission was to completely and totally alienate a woman that put her trust and faith in you on a first date (trust that you won't kill her, faith that she'll have a decent time with you), how would you go about it?

Of course, there's the obvious tactics.  Eat with your mouth open, talk constantly, watch SportsCenter the entire time. Those choices are so simple they don't even deserve to be expounded upon.

No, I wanted to go a little deeper. I thought about writing this as a numerical list of the best ways to achieve full alienation but ultimately scrapped that idea after realizing that none of these are really better than any other. They're all good. Which is to say, they're all bad.

Go Out Late For Several Nights In A Row Before The Night Of Your Date

I actually did this recently, but not on purpose. Wednesday and Thursday nights of the week I had a Friday night date I went out until around 2 or 3 a.m., only to have to get up for work by 7 a.m. By the time Friday night rolled around, I was beyond exhausted but the prospect of eventual intercourse excited me enough to at least pay for a few rounds of drinks with a girl I had (at best) limited interest in from

Beyond the facts that I wasn't attracted to her physically (the photos, frankly, could very well have been of someone else, but that's for another article) and the conversation was numbingly mechanical, I was exhausted by 10:30 or so for obvious reasons.

No matter who was talking, I couldn't stop yawning. I'd given up apologizing and explaining each one, despite internally trying to stave off the inevitable.  Eventually, I couldn't fight it any longer.

I wouldn't say I fell asleep, per se. It was more like one of those long blinks, the ones where your chin hits your chest and breaks your stupor long enough to realize: Hey, I don't recall anything that just happened, I must have been asleep.

Nothing more flattering to a woman than falling asleep during one of her stories. Trust me.

The Reverse Bill

When the time comes for your check, be a gentleman. Take it before she can even sneak a peak, push it back towards your date once you've satisfied your curiosities, and confidently say “Don't worry, I'll get the next one.” Girls love confidence, so I've heard.

That'll make her think twice about that nauseating “Oh come on, let me leave a little bit” line. Then again, nothing's worse than the staged hand-in-pocket/purse move that might as well be one of those fake cabinets in your kitchen that never opens.

Ask Her Out To Dinner

But don't meet her out until you've already had a satiating meal of your own. Without her.

Upon arrival at the pre-determined bar or restaurant, simply explain that you forgot you were meeting for dinner (Note: For this method to work best, it's preferred that you set up the dinner date within 24-48 hours of the actual meeting). Continue to explain, without expressing even the slightest hint of remorse, that you should still proceed as planned and that she should definitely still have dinner. No, you aren't hungry at all any longer, but you wouldn't want to stop her from eating.

Order For Her

If that last one isn't your speed (if this article was a college course, that last one would be for advanced students only), try actually taking her to dinner but don't allow her to order for herself. There's nothing a woman in this century loves more than being told what to do and what to eat by a man she just met.

You can go one of two ways, depending on how big of a dick you feel like being. After you're done placing your order, pause for a second as if you're actually going to let her order for herself like the adult she is. Then, a word (or even a syllable) into her order, cut her off and ask for either an enormous, fatty meal or its polar opposite. Either go with the steak and loaded baked potato or a side version of the house salad with dressing on the side. Personally, I think the latter choice is the best one, so far as alienation goes but as our friends from Legends of the Hidden Temple said, “the choice is yours, and yours alone.”

Allow For Flexibility When It Comes to Scheduling

Work to find a time for a first date when you have friends from out of town coming in and staying with you. Instead of being a bad friend, bring one of your old pals on the first date with you. Bonus points if that friend is a girl, even better if that girl is hotter than the one you're on the date with, and best if that girl is your actual current girlfriend (Note: In the history of civilization, the last version of this move has never been successfully pulled off and not for lack of effort of the male species.)


Being comfortable on a date is of the utmost importance. I don't care if you went to private school since you were a zygote, there's no way you feel better in a pair of khakis or pressed jeans and button down than you do in a baggy, worn t-shirt and sweatpants.

If she can get away with a soft, flowing dress and yoga pants, why can't you be comfortable and thus cagey of your less-than-desirable physical attributes.

So, that's my list. Of course, there's more obvious ones like the timeless “flirting with the waitress (or, any woman you're not on the date with)” move, showing up incredibly late, saying awkward things (When did you first get your period? My sister got hers at 11, was that normal?) or talking exclusively about other dates you've gone on recently and women you can't wait to see again.

None of those are bad and trust me, they'll all work wonders, but is it fun to do what everyone else has done? I say, if you're going for alienation, go for originality as well.

Scott Spinelli | Elite.

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