The Holiday Dating Gift Guide

Sometimes the man in your life is the toughest person to shop for. Is the gift too much? Too little? Too weird? Fret no more, ladies!  We’ve got your handy guide to what to get him, based on where you stand.

Charli Penn Dec, 10, 2012

1 of 17 Getty Images

Wondering what to get the special man in your life? We know that shopping for him can be hard, especially if things are, um, well, "complicated" between you. What do you get the guy you're in love with but he has no clue? Or what about the guy you just started dating and really don't want to scare off by overdoing it? Not to worry. We've got you covered!

2 of 17 Fossil.com

Stop admiring him from afar and show him a little love this holiday season with this professional -- yet sexy -- gift idea. The Estate iPad Easel ($75) holds nearly all of today's popular tablets and comes in three man-friendly colors. It's the perfect way to mix business and pleasure!

3 of 17 Amazon.com

You don't have to spend a lot to impress him this season. Leave a nicely wrapped box of Apple Ear Pods ($29) sitting on his desk and watch him smile when he opens it. It's more thoughtful than socks and less scary than cooking classes, making it a sensible gift and a safe bet if you'd like to remain cautious with your approach. (Wink!)

4 of 17 Wine.com

Unless he doesn't drink (in which case we recommend sweet treats instead), you can never go wrong with giving a man a wine set for the holidays. We recommend the Holiday Sparkling Wine Trio Gift Set ($39) because it's festive, has a nice variety and won't break the bank. (Psst: Slip a note in the box hinting that you should pop at least one bottle together.)

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You've gone on a couple dates, and there's definitely chemistry between you. Now that the holidays are here, you'd like to add him to your list, but you don't want to appear too pushy or too invested. Does this situation sound alot like your own? Head on over to a popular deal sites like Groupon, Gilt City, of Living Social and purchase a romantic dinner deal for two. Send him the voucher with a flirty message that reads: "Happy Holiday!" and sign it from "your dinner date." He'll be impressed.

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Whatever your situation at the moment, he's sure to walk away with warm thoughts of you when he unwraps this sexy, cozy SFLAIM Scarf from Diesel ($78). Cuddling just got more comfy. You in?

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When things are “complicated” between you, you need a gift that’s unique enough to be memorable but not personal enough to mean more than you’re ready to say. The Chrome Clocky Alarm Clock ($55) is the perfect pick. The crafty little clock jumps up and rolls around the room to hide from you when it’s time to wake and you’re dying to press snooze. Plus, it’s a surefire way you’re the first person on his mind each morning.

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Now that things are official, you’re going to be making lots of amazing new memories together. Capture the sweetest moments of date night in real time and go home with the memories in your hand with the Polaroid Compact Instant Analog Camera ($69). It’s the modern version of the classic camera you loved as a child and just cool enough for him to love now.

9 of 17 Amazon.com

Normally a fitness gift might send the wrong message to a guy. (You know, like, you think he should hit the gym harder.) But, for the guy who's only focused on impressing you – like your new boyfriend! – there’s  no way he won’t love The Perfect Pushup Counter ($10).

10 of 17 JCrew.com

Send your man to work in style for the New Year with this chic and modern Billykirk for J. Crew Limited-Edition Bike Messenger Bag ($288). It’s handcrafted and super handsome. He’ll love it, we promise!

11 of 17 GrillingGifts.com

No man can resist a grill, and nothing will make him happier when he gets there than to find something special waiting just for him. These Personalized Leather Grilling Gloves ($29) will be the first thing he goes to grab when summer grilling season begins again.

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He made your heart skip a beat when he surprised you by popping the question, and now it’s your turn to blow him a way with an equally exciting thrill. Give him the gift of the unexpected with a once-in-a-lifetime experience gift in your area from Cloud9Living.

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Sure, men aren’t supposed to play with toys anymore, but if you get your fiancé this Numark iDJ Live DJ Software Controller ($84), he’ll be like a kid in a candy store on Christmas morning. Plus, it's compatible with his iPad or iPhone and easy to transport.

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You married a unique and wonderful man. Shouldn’t his gift this Christmas be the same? Wow him with this Natural Wooden Watch from Red Envelope. It’s hypoallergenic, chemical-free and features a jazzy red face made of mineral crystal. He’ll be happy to head back to the office and show it off.

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If you’re like most wives, all the décor in your home thus far has been 100-percent your call. Well, that stops now. Throw him off this holiday season with a piece of furniture he would have eagerly chosen for himself – this Flip-Front Mini Bar ($99) from Target that holds the wine and the whiskey in one chic compact corner. Cheers!

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You weren’t quite right as a couple, but that doesn’t mean you don’t still care. Being friends after a breakup can be tricky, but these “cool” little Stainless Steel Ice Cubes ($24.95) will surely break the ice.

17 of 17 UrbanOutfitters.com

If you haven't forgotten his shoe size, slippers are always a sure gift for any man. And, in this case, they're familiar but not too personal – just the kind of gift an ex might expect. These Minnetonka Double Bottom Fleece Moccasins from Urban Outfitters ($48) won’t disappoint.