Have you ever had fantasies about or plans for sleeping with your best friend’s mom? Of course you haven’t. Because even if you had, you wouldn’t say so. But assuming – purely hypothetically of course – that this is something you had in mind, Mother’s Day may be the best time to make your move. Why? Because when everyone else is buying the object of your desire new kitchen doodads, digital picture frames, and a crappy brunch at Appleby’s – making her feel older and more mom-like than ever – you’d be there with everything she really wants, which is just to still be appreciated for being a woman. You dirty, exploitative bastard, you. Shame.

This Is Not A User Guide

First off, let’s get a few things straight. That’s not a typo in the headline. It is in fact MYLF, not MILF, because of the first-vs-second-person pronoun involved. It’s YOU that has an “M” you’d like to “F”, not us. We’re just here to help. Second, we’re only here to offer help with gift ideas. If you need help actually accomplishing your goal, you’ll need to look elsewhere. Not surprisingly, there are guides provided by sleazy “bro” websites, like Mademan’s How To Have Sex With My Friend’s Mom, or BroBible’s 13 Steps To Banging Your Best Friend’s Mom In No Time. Apparently Quora won’t be much help here. Nor will Yahoo.

Preparation

In the event that your personal character is deplorable enough that you’re thinking of trying to seduce your friend’s mom who’s still married, we have two things to say: 1) You’re disgusting. And 2) That is not necessarily an obstacle. We’d just recommend two pre-holiday gifts. Nolo’s Essential Guide to Divorce, and Paul Simon’s 50 Ways To Leave Your Lover.

Mood Music

This of course depends on the ages involved, so these are just some basic ideas to get you going. The concept is that you want to pick music based on when the recipient of your, um, “affection” was in her early twenties, and maybe still a little wild. Was it the seventies? Then maybe Fleetwood Mac. The nineties? Maybe Mariah Carey. If it was the eighties, maybe some Prince. Scratch that. Prince would probably work for ANY era. These aren’t gifts for her, they’re props for you. Make sure you have them randomly playing whenever she’s around, and maybe let the Fleetwood Mac CD fall out of your backpack “accidentally” in her view. Music is a powerful trigger, even when it isn’t actually being played.

Subtle But Not So Subtle

Let’s face it. When you want to sleep with someone, all subtly seems to go out the window. And a ridiculous and inappropriate pursuit like yours will be fraught with all sorts of passive-aggressive overtones. But when you finally get around to laying your entire life and reputation on the line with some kind of advance, it won’t hurt to have dropped some clues. These can range from the suggestive, to the over-the-top scandalous. In fact, the latter might work better, by pushing the boundary but leaving you an exit route like “It was just a joke! You didn’t think I was serious, did you?”

Announce What An Opportunistic Gigolo You Are

No-one can directly call you out on these, but wearing them sends a definite signal.

Flattering But Corny Messages

Relatively harmless, but flirty. Expect to get beaten up anyway, if she has a husband.

A Little More Brash

This is creeping (seems an appropriate word here, no?) into dicey territory. You could still play them off as gags, because they literally are gag gifts. But that guy who beat you up for the Just Do It T-Shirt? He’d probably run you over with his 4×4 and “disappear you” for these.

 

The Point of No Return

The 16GB Duet Lux Vibrator is sort of the last “stealth” gift on our list. No, we have NO IDEA why someone would build a 16 gig thumb drive into a sex toy, but it works here for a few reasons. First, it’s still stealthy, in that it looks more like a wireless device than a sex toy. Second, it would allow you to put all sorts of saucy files on the thumb drive, if you were clever. And perhaps most importantly, the damn thing costs over 300 bucks, so will show your commitment to the venture.

Abandon All Hope

For the rest of these ideas, it’s pretty much all or nothing. Show your willingness to be her sick little baby man with the Pink Prank Pacifier. You’ll have to take it out of your mouth long enough to tackle the OMG Candy Bra though. The Loveryoyo Slave Passion Love System is about as committed as you can get to a scenario like this, but just to throw a little maternal behavior back into the mix, give her the Trojan Dash Button to let her know that if she takes care of the shopping, you’ll take care of her.

 

Or Maybe Deal With Your Mental Problems

While it’s not exactly “Oedipus Complex for Dummies”, The Oedipus Complex: Solutions or Resolutions? claims to be written in lay terms that anyone can understand. Maybe it could save you a lot of time, money, and savaged relationships.