ILY’s Holiday Gift Guide For Every Type Of Situationship

The holidays are here and there’s no longer time on the clock to bounce around the “to gift or not to gift” question. Whether it’s to impress potential in-laws or just to say “thank you” for a year’s worth of Netflix & Chill, ILY asked around for the best finds to wrap up for your situationship this season, regardless of how (in)significant the relationship may be.

Art by Sam Liacos.


1. You’ve only been on two dates, but here come the holidays.

“Two dates? That’s nothing! For something like two dates in, I would say get them a workout class that they also have to go to with you. Either Rumble or Soulcycle. I feel like there is no judgment for guys to do either one. That way, you’re ensuring yourself at the very least some burned calories and also a third date.” Danielle Prescod, Editor at BET.com
Rumble Boxing Class – $34
Soulcycle Class – $34

2. You two are pals with potential, toeing the line between friendship and a little more.

“I’m buying the girl in my situationship some form of information and media—a book, a magazine, a DVD box set. Something to enlighten her on the way I want our situationship to sway. If I want the situationship to be a relationship, I’m getting her a subscription to Office mag or POPEYE mag. If I want it to deescalate, XXL.” Keith Charles, Rapper

Office Magazine – $20

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3. You guys are friends with benefits and perfectly fine with it.

“That sounds like a beautifully packaged bottle of let’s get it poppin.’ That sounds like you come in with, not a bottle of wine from Trader Joe’s… Maybe a nice wine and spirits spot and get something that’s going to make what you guys already do a little bit more special. I think even champagne is nice, honestly. If you’ve been saving throughout the year and you can get a nice bottle of Moët. Or Martini & Rossi. It makes what you’re already doing a little bit more festive for the holidays, but doesn’t take your relationship out of context. Premium alcohol, nothing more, nothing less. This is not a smash and dash situation. The great thing about friends with benefits is the conversation that can linger way after the sex has paused, so you don’t want to come through with nothing but your private parts because you actually care about this person. The friends part came before the benefits part, so you want to acknowledge that but not to the extreme.” Tracy Garraud, On-Air Host at Sway in the Morning

Martini & Rossi Asti – $11.99
Moët & Chandon Imperial Brut – $48

4. So, are we dating or…?

“I’ve met a lot of guys who don’t drink cocktails but want to venture outside of their ‘whiskey-ginger’ box. W&P Design has a super cute ‘carry-on cocktail’ kit. The old-fashioned is like a gateway drug to cocktail drinking. Buy two and let him serve you, too.” Jillian Tuttle, General Manager at New York’s Public Hotel

Carry-On Cocktail Kit – $24

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5. Congratulations, whatever murky exclusiveness you had going on has been upgraded to a formal boyfriend/girlfriend title.

“I’d buy him vanilla Tom Ford Beard Oil because I really liked the smell and it’ll soften his coarse ass beard for making out. Basically something that will benefit me in the end.” Mikelle Street, Writer/Editor

Tom Ford Beard Oil – $52

6. It’s an early anniversary (or month-aversary, perhaps), but it falls right around the holidays.

“Oh, that’s a hard one. I would go with an experience they’ll never forget. Perhaps a two to three day getaway to the Bahamas that gets you out of the cold weather. It would be both an anniversary and Christmas gift. The Christmas gift would be smaller than the vacation package for the anniversary. I would give a present hinting to the anniversary getaway like new trunks and sunglasses or something related to the trip.” Sabine Milien, Lifestyle Coach

Groupon Vacation Packages – Varies
Gate1 Travel Tour Packages – Varies

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7. You’ve got to meet and impress the parents, the first major step in becoming part of the family… hopefully.

My ex is Dominican, so I work at Oscar de la Renta and last year we had a press event for a collectable stamp. It’s Oscar’s face and some prints from some gowns. I got them a booklet of the stamps and gave it to them in a tin from the event. To Dominicans, Oscar is like god. It’s crazy how much they love Oscar. They really liked that. It was part of their culture and they could relate to it. But in the future, I guess I’d find out what they’re into and then get them something like that. If the mom likes to cook, get her stuff from the kitchen. The dad, if he’s handy, get him something like that. Or tickets to a game for the both of them so they can enjoy that. Steve Jackson, Photographer at Oscar de la Renta

Oscar de la Renta Ceremony Momento Stamps – $21.95

8. While you’ve been happily together for a while, neither or you are quite ready for the big leap of marriage.

“If you’ve been dating someone for years, you should already know your boo’s likes and dislikes like the lyrics to ‘Jingle Bells.’ I’m a fan of experiential gifts, like sports game or concert tickets or booking a weekend getaway. Another option is to create a personalized gift basket with one item that he/she may have wanted for some time or caters to their obsession (I once received a Wonder Woman backpack for this reason), a few items that may be a nod to an inside joke or a great memory, and another item that involves an activity of some sort, i.e. has your significant other been wanting to whip up food at home more? Book a cooking class for the two of you. Honestly, the best gifts to give while in a relationship are the ones that require effort, thought and heart.” Adelle Platon, ‎Editor, Culture & Content at TIDAL

NBA Game Ticket – $179-300
Cooking Class – Varies

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9. In the midst of that post-proposal high, is the “Yes” and ring combination enough of a gift?

I just went through this. Yeah, I would still give a gift. Maybe an iPad or a bag? I would also consider giving a gift card. You can’t go wrong with a gift card, depending on the store or who your girl is. Maybe a little gift card to Victoria’s Secret for both parties to be happy. Something that they would appreciate. Carl Lamarre, Hip-Hop Editor at Billboard

iPad 9.7-inch – $329
Victoria’s Secret Gift Card – Varies

10. Even after the break up, you two are still best friends (or so you say).

“A bottle of wine… you know, to drown the sorrows because you’re not with me anymore. I’m just kidding. This is because I know they like to drink and have a good time. It’d be a red wine, a good dinner wine, because the person in question likes to eat well, eat good. Like a Malbec or something like that, it’s good with steak.” Avery Green, Digital Sales Manager at Hot 97/WBLS

Pascual Toso Malbec Alta Reserve – $43