Tips for Gifting the New Boyfriend

By: Joe Thompson

Buying the right holiday gift for your guy can be dicey. If it’s too serious you’ll scare him, too silly and he’ll think you don’t care—and just imagine what will happen if your present is too sexy, too expensive, too cheap, or too intimidating. In short, the token that’s supposed to let him know you care could send him running for the hills.

But find the right gift? Well, then, you could be setting yourself up for many more years of holiday fun.

With that in mind, we asked a number of men in long-term relationships for their suggestions on buying the appropriate gift depending on how long you’ve been dating. Here’s what they offered:

Most guys feel some anxiety about what to buy. Talk about it, and set a limit on how much you'll spend. “My husband and I still do that to this day,” says Marcus, who’s been with his man for 12 years. “It gets us excited about the holidays, sets up a fun challenge, and lets us think about things we want to do in the coming year.”

“No matter our budget, we always get one another stockings because they feel like one big gift, but they’re really simple and relatively cheap,” says David, who is in a three-year relationship. He suggests buying candy, condoms, travel lube, and individual bottles of champagne or alcohol. “Then I get one or two nicer things, like an iTunes gift card, a Kiehl’s bath product, or a treat he wouldn’t normally eat. I don’t care what your age—stockings are fun.”

Gifts at this stage should be cute, fun, and romantic, but not too sexy or expensive. Let the guy know you care but don’t be so serious that you freak him out. Zach, who’s in a six-year relationship, says, “On our first Christmas Ted got me all the Weetzie Bat books because I said I’d loved them in junior high. I’d only mentioned it once in a random conversation, so this gift showed me he’d listened.”

GET: A hard-to-find version of his favorite movie, copy of your favorite book, framed picture of you two together, a nice bottle of wine or alcohol, or a cute T-shirt.

Go for something substantial, sexier because the heat is revving up, and family friendly if there’s a chance it will be opened in front of your families. “I got Randy a leather harness but made sure he opened it in our hotel room,” says Derek, who’s been with his man for two years. “Only go for a sex toy if you know they’re into it. Christmas isn’t the time to spring new fetishes on your boyfriend.”

GET: Any of the 1-3 month gifts. Also try massage oil, candles, and couple’s events like a wine tasting, spa day, or workout/training session for something you guys are excited to try.

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Go for a bigger gift and spoil him. “At this point I knew Derek’s personality so I could get him a couple fun gifts and then one big one: a trip to San Francisco,” says Randy of the aforementioned leather harness. “We lived in Los Angeles so it wasn’t that expensive, but since it was a trip it felt really important.”

GET: Besides an easy weekend trip, try a nice jacket, designer jeans, man bag/satchel, or tickets to an upcoming concert or show.

You’re coming on the time when you either commit or bail. Kinky clothes work because it never hurts to spice up your sex life. “At a year we felt like we were building a life together,” says Marcus. “We started buying things we knew the other wanted for his apartment, but it was also setting the foundation for us living together.” 

GET: More personal items like a nice wallet or sunglasses, lessons for something he’s wanted to do, a game system or something you can play together, pricier tickets/trips.

•Know what is and isn’t his style. Ask causal questions like, “How come you never wear flannel?” before buying him that shirt.

•Know his size. Don’t insult him with something too tight or too big.

•Don’t buy him “single guy” gifts like porn, a generic gift card you bought at the grocery store, fake poo, etc.

•Avoid gift sets that look cheap or re-gifted. It’s better to make up a pack of many different items to show you care.

•When getting a gift card as a major gift, make it for a place you would never think to go— a restaurant, store or event that let’s you both have a fun/enjoyable experience.

•Nose hair trimmers, while useful, are insulting. Don’t get him one for Christmas.

Illustrations: TOM OF FINLAND, (Finnish, 1920–1991), Untitled (Santa), 1987, Pastel on paper, ToFF #87.27, ©2009 Tom of Finland® Foundation