How to choose the perfect gifts for every stage of your relationship

It’s always stressful to start dating someone new weeks or even a couple of months before their birthday. What’s the gifting protocol? How much do you spend? What do you give?

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Holidays can be equally stressful for newly minted couples. How much do you spend? What do you give? It’s too soon to spend a lot of money. You likely don’t know each other enough to know what they have always wanted. But you can still get them a gift that they will love, that means something, and that will even give you brownie points for being so awesome.

The biggest holiday gift mistake made is lack of communication

How important are the holidays to your partner? How have they historically spent them? Ask questions and tell stories about what the holidays mean to each other and what your favorite holiday memories are. How do you spend the holidays? Not only are you learning more about your partner, about their family, friends, traditions, and values, but you are also learning their preferences when it comes to gifts – both giving and receiving. Talking about the holidays can be very revealing.

The second worst holiday gift mistake made is lack of thought

More than anything else, your gift should be thoughtful. As you are talking about the holidays, you can even ask what their favorite gifts are that they have received over the years. Again, you are collecting information. Do they value experiential gifts, the gifts of time, or a certain type of present? This doesn’t mean that you need to ask: “What do you want for the holidays?” But if you listen you will be able to come up with at least a preferred style, and from there you can select something that has the highest chances of them loving it.

So what do you give?

The gift of time and shared experiences can be the most cherished gift of all. Buy a couples spa treatment for you both. Plan a weekend away at a local hotel. Go kite surfing or kayaking. Organize a trip to New York and go skating in Rockefeller Center. Arrange a hike with a picnic at the top. But don’t just give a random experience or one that you really want. Give something that they really want, but you can do together and enjoy. When you give the gift, write a card that explains the itinerary, why you want to do it together, and give a little gift that embodies the experience so that they also have a wrapped “present.” Because everyone likes a little something to unwrap.

It’s not “just the thought that counts” if you put no thought into it, and that’s expressed in the card. So the gift is threefold of a wrapped present, activity and card.

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Give them a playful/thoughtful stocking

Give him a stocking that is thoughtful and reminiscent of happy childhood moments. Then fill it with little symbols that you care, want to take care of him, pay attention, get him, and encourage his happiness.

A few suggestions:

For the handyman: Stepless Ratchet Tool
For the guy with a strained family dynamic: Family Time is Hard wine
For the guy you want to love (or want to love more deeply): The Love Game: 36 Questions for Falling in Love
For the quirky (or sock loving) guy (or for the guy warms your heart so you want to warm their feet): Awesome Socks! These are the best from Out Of Print.

For your new boyfriend

You just started dating “officially” in that you aren’t dating anyone else. You consider him someone who has real potential and you want to explore it. Don’t buy him anything that’s too much. And I mean “too much” in that it’s too expensive, too sentimental, or too intrusive. Give him something sweet and thoughtful, and also low key. This is an opportunity to show him that you are more than just fun, sexy, and exciting. Show him that you should be considered as someone who has real potential too. Show him that you want to care for him and take care of him. Make him dinner. Even if you don’t know how to cook, you can pull this one off. Simply go to a high end market and buy a simple dinner that you doll up with extra special sauces plus a fun drink or bottle of wine. Of course you also want to have something wrapped up for him under the tree, and that will be cooking equipment as well as a holiday card that describes the experience that you are about to give him.

The card:

Let him know how taken care of and cared for he makes you feel. Let him know that you want to do the same thing, but in your own way. Then include an “invitation to dinner” which will include the date, time, location, and menu (if you’d like).

The menu:

Choose something simple and delicious that can be prepared ahead of time. I love the book Cravings by Chrissy Teigen. Pizza or burgers are simple but can also be simply delicious. You can also design a specialty cocktail.

The wrapped gifts:

Cuisinart Food Processor: You’re going to need this if you make homemade pizza dough.
Griddler: It’s a cleaner way to grill burgers – delicious and minimizes the mess.
Bicos Water Goblets (Set of 4) by Vista Alegre
Love Who You Want Coasters by Christian Lacroix: They are fun and quirky and will be your special coasters that always put a smile on your face
Heart Shaped Ice Trays: Because a drink is just a drink until it has a heart ice cube in it!
Silicone Pizza Mat: You’ll need it to make your pizza look a little less amateurish

For your new love

There are plenty of ways to spice it up that have nothing to do with sex. Though, they may lead to sex. It’s time to experiment, explore, and break down some barriers.

The card:

“I have loved getting to know the various sides of you. I feel like there are more that I want to explore. Let’s get deep and dirty together.”

The wrapped gifts:

5 Love Languages: The book is an essential for all new serious couples. It will help you to love him in a way that he feels your love, and lets him know how to love you in a way that you will feel his love too.
Make a lasting imprint: Literally, get naked and roll around in paint, leaving your prints on a gigantic piece of paper. The outcome can be clear images of your bodies, or you can be more discreet and simultaneously more exciting as you create artistic images of your entwined bodies while making love – making it your secret that the beautiful impressionistic painting hanging on the wall is actually your naked bodies. The Love Is Art package has all the materials needed to ensure a safe project, including a large plastic sheet to protect the floor, white cotton canvas, non-toxic paint, and even two pairs of disposable booties so you can walk to the shower to clean up without leaving a trail of footprints.

The person you’re ready for something real with

You want to move in together – you’re talking about him moving in or buying a place together. Show him that you’re really ready for real by buying a statement making gift, and having an experience on it. In fact, make an evening of it. Enjoy a night in bed. And I’m not talking about just sex. I’m talking about having real and deep conversations. Use the 36 Questions for Love as conversation starters. Order munchies and enjoy dinner in bed. Then break it in. The mattress I mean.

The card:

List all of the things that you love about him and why. It’s the “why” that makes this card meaningful. It’s not just that he buys you watermelon gum every time he’s at the gas station. What that shows is that he thinks about you even when you’re not there, and not only does he think about it, but he shows you that you were on his mind because he thought to get out of his car and buy your favorite childhood flavor of gum that brings out the fun, carefree youthful side of you that only he has the ability to bring out. Then tell him that you want to move forward in your future together, and so his gift starts tonight (or whatever night works for a dedicated evening) and will last all night. It’s time to break in a new bed together and move forward in the future with a fresh start.

The wrapped gifts:

A gift certificate for a food delivery service
A printout of the 36 Questions for Love
A new mattress that has zero lingering impressions from past partners. A new mattress is statement making. It says that you are cleansing yourself of your past and ready to move forward with him into the future. Put the new mattress on the bed and tie it up with a big red bow.

For your longtime love

You want to give him a gift that is sentimental. Something different. Something that will show him that you love you two and that your memories are precious to you. And something that says that you want to make more memories together.

The card:

The card will start with a list of vacation memories. Don’t just list locations. Actually write out one or two sentences describing a particularly memorable moment from several trips. Then finish it by describing your next trip, which you already booked for a weekend. Or include a custom gift card for an Air BnB to the town of your combined choosing, where your next couple memory-making adventure awaits.

The wrapped gift:

101 Nights of Great Sex by Laura Corn: Get ready to explore a very sexy side of your relationship with these experience invitations.
Gifted Custom Art: Remember that time when you two went on a camping with your black lab when you just started dating, and the three of you explored tide pools (and you got in trouble for having a dog and a beer, on the beach)? Take the photo of the three of you on the beach and paint it by numbers like you used to do when you were a kid. Send the picture to Gifted Custom Art and they will turn it into a paint-by-numbers (which makes painting easy for any adult) outline printed on a 16”x 20” gallery wrapped canvas. The kits come with everything you need (paint, brushes, easel) to create a beautiful piece of custom art.

The point is that your gift is meant to be more than a present. It’s an opportunity to deepen and expand your relationship. Happy gifting!

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