Holiday Break Challenge: Bringing Home a Chick You Went to High School With

The top-to-bottom evaluation kick-starts the conversation — does she look worn down, has she added weight, is her butt bigger or smaller, etc., which ultimately ends in at least two or three bros claiming they can accomplish something they never got to do in high school and bring home the chick you’ve all spent the last 15 minutes over-analyzing.

The harsh reality in this situation — as it is with most situations you will face, so get used to it — is that it’s easier to say something than it is to actually do it.  Couple that with the fact you will never be able to relive your high school glory days no matter how hard you try — trust me, I’ve tried — and you’re rate of success is already plummeting to around the 10% area.

Factor in there’s a good possibility she has a boyfriend or, worse, may no longer be into dudes — sorry bros, but this happens — and now you’re looking at about a 3-5% success rate.

If the odds weren’t stacked heavily against you already, you also have to jump over these hurdles:

Bringing her back to your former home, i.e. your parents place

For one, this challenge requires a designated driver if one or both parties have been drinking and the bar is several miles from your home, which it most likely is if you grew up in the suburbs. This dilemma ends up creating a problem within a problem, because who really wants to be your booty call chauffer for the night when they’re only home for three or four days?

Also worth mentioning, I don’t know any chicks who get wet from the “let’s go back to my parents place” line, but if you know of any, please send them my way. Finally, even if you’re to pull off this Christmas miracle by finding someone to drive you home, convincing her to come with you, and finishing the job in your old bed, then the question remains what do you do with her afterwards?

Best case: you both really enjoy the sex and laugh about why it took you so long to do the deed. Worst case: she wakes up in the middle of the night, doesn’t remember coming home with you and screams the R word. I don’t know anyone personally who this has happened to, but is there really a worse possible outcome?

Why, yes, there is. Mom or dad could come knocking in the morning and stumble in on your sleepover.

We are getting way ahead of ourselves here, though. If you’ve managed to make this much progress and completely conquered this challenge, then you’re in the top 1% percentile of all bros — congratulations! — and that’s because….

She knows everything about you

Not to mention, her friends do too, leaving you at a complete disadvantage compared to meeting some random college girl out at a bar and convincing her and her friends that you are harmless and “kind.”

Remember, this is a chick you spent the four most awkward years of your life with and her judgments of you were written in stone a long, long time ago. Unfortunately, it’s impossible to unfreeze concrete, which means, even if she forgot that you hooked up with one of her friends junior year — trust me, she won’t, then you’re still fighting an uphill battle.

No matter how much you’ve refined your game over the last couple of year; no matter how many hours you spent in the gym, nothing is strong enough to lift her preconceptions of you. The image of your gawky, pimply 16-year-old face is engrained in her head. You could look like Brad Pitt and she’d still be seeing Screech.

Side note: You may be reading this, huffing and puffing to the tune of, “I know everything about her, that’s the real problem.” That maybe true, but it’s not going to make getting laid any easier. Regardless, all that knowledge is like a pit of quicksand.


It was so much easier to hook up with chicks you went to high school with, when you were in high school, because they didn’t know anything about the world and had yet to experience life outside the bubble. Now, they’ve been with all sorts of different guys and have refined what they like into a specific “type,” and if you don’t fit into this category you are going to have no option but to give yourself a nice long tug when you get home.

On the flip side, chances are that if she found you attractive in high school, then she probably still does; however, a simple physical attraction won’t end up getting you laid like it used to when you were seventeen. You’re going to need to connect with her on a different level and that means a lot of hard work will have to be done in a short period of time. I’m talking about really impressing her with your approach, your pick up line and whatever conversation you can generate without coming off like a complete douche.

Speaking of douche…

High school parties no longer exist

I wish they did because it would be a lot easier for all of us bros to get laid if life never advanced past the age of eighteen. See, in high school — and a large part of college, too — you can get as obliterated as you wanted and act however the hell you want to act and still be rewarded with pussy. It still amazes me how easy it was to get laid when you acted like a complete dick, because that’s all chicks want when they’re in high school and they don’t know any better. Eliminate this naïve behavior and replace it with a heavy dose of sophistication and exploration, and you realize that the obnoxious attitude that you once used to score with regularly is as outdated as having a bomb shelter in your basement.

Even if — and I am trying to present a counter, positive perspective to all of these negative situation — you find yourself at a house party in your hometown, you’re still going to run into the aforementioned problems on this list. You can try and relive the good days with your buddies, and I hope that you do, but I’m willing to say there’s about a 2% chance of you landing a piece of strange ass in the process.

With that said, flash forward to the present scenario, and your greatest obstacle from back in the day is still standing right next to you…


Childhood friends are the people you grew up with; the people you know the best in the world, besides your family members; and there still the same old jerks that prevent you from getting a late the majority of nights.

Although it’s not fair to blame your bros for your inadequate sex life or sexual misadventures, it does seem justifiable to place some sort of guilt on them when specifically talking about having sex with a chick you all went to high school with, because whatever she thinks of you (see: she knows everything about you), stems directly from what she thinks of your group of friends — and it’s probably nothing too positive.

If this hypothetical chick has always gotten along with you and your bros — no matter how dim-witted your high school behavior may have been, then you enter a different reality, but one that has a similar result. Chances are if this high school friend, who so happens to have a vagina in between her legs, has tolerated you and your buddies for this long, then more than one of you will try and have sex with her.

As flattered as she may be from this attention, and probable groping, all your individual efforts will end up canceling each other out and your bro pack will still be stuck on square one with beers in your hand and no pussy in sight.