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Underwear is a staple gift. Victoria’s Secrets across the country suddenly find themselves flush with awkward first-timers all-too-willing to shell out loads of cash to get something shiny, sexy, and usually not even a little bit comfortable. And sometimes, depending on how well the underwear-giver actually knows their Valentine, it can be more than a little awkward! There’s a large gulf between “be my Valentine” and “be the tailor to my genitals.” That’s not to say that underwear is a bad Valentine’s Day gift. On the contrary! But if you’re gonna risk it (and hey, with great risk comes great reward), consider what level of underwear giver your relationship might actually be ready for. Below are a few tips based on what level you’re at with the lady or guy in your life, from Level 1 for those wise enough to tread with caution, to Level 3 meaning you’ve already thrown caution to the wind along with the rest of your clothes. 

For Her:

Level 1: Boyshorts

When you want your lady to know she is your superhero, defender against all things zombie, and totally the sexy tomboy of your life. While there’s nothing inherently unfeminine about boyshorts, they do give off a certain kind of Hollywood heroism that may be a safer bet if it’s your first time buying clothing for your better half’s lower half.

Level 2: Cheeky Briefs

A cheeky gift in the most British of senses, you won’t be fooling anyone when you buy your special lady a pair of cheeky boxer briefs, but by avoiding going for the sexiest option possible, you’ll be more likely to get the intended reaction of a bit of cheekiness in return. Cute, sexy, but still playful.

Level 3: Modal Thong

So you want to give something sexy as hell, but you are empathetic enough to understand that G-strings are just terrible. Something with the name “string”should not be considered clothing. So if you you still want a gift that is explicitly designed to have your “baby move your butt, butt, butt,” then to further quote the famous late 90s poet Sisqo, the only gift for your Valentine is “that thong thong thong thong thong.”

For Him:

Level 1: Lounge pants

Sweatpants aren’t sexy, but a nice pair of lounge pants, on the other hand, definitely send the right message to the special guy in your life. They say: you’re my lounging commando. Telling your Valentine you’re a-ok with being lazy and comfortable with them doesn’t have to come at the expense of sexiness.

Level 2: Fitting Boxer Briefs

To tell your man even more explicitly you care about his junk even when you’re not directly involved, get him a gift that will make him wish his new date underwear was his daily underwear. Boxers or briefs? The question is absurd. Get him the combination that he’ll want to show off when he can and that will support him when he can’t.

Level 3: Thong

Perhaps it’s a gag gift. Perhaps your man deserves to feel like a very pretty lady. Or perhaps it's his punishment for singing The Thong Song way too many times. You can either give him a pair of yours, or you can order him a thong that might actually be comfortable to a guy who can feel comfortable in a women’s thong. It’s a Level 3 gift for sure, but it’s not necessarily the wrong one for the right guy!

By Andrew Hendricks

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