Hit a Gift-Giving Home Run

The holidays (or anniversaries, birthdays, Mother’s or Father’s Day, Valentine’s Day) are theoretically times for thoughtfulness, creative self-expression in your gifting, generosity, receptivity, gratitude, and joy and intimacy all around.  

That’s the point, right?  

But the lived experience is often really different from all that.  Especially if you’re male, maybe you’ve wound up feeling pressured, shamed… Feeling like you failed, feeling discouraged, thinking “why do I bother?” maybe even thinking your partner is impossible to please… I get it.  

You’re not alone! 

I’ve worked with many people for whom gift-giving is fraught, and I’ve discovered some keys to finding a way to win.  In this post you’ll learn:

  • Why gift-giving in relationships can get so frustrating

  • The mistakes that lead to gift-giving  misery

  • And what you can do to feel successful, to have your partner feel loved, and to be closer than ever after this holiday season

Important note: In this post, I’m talking in a gendered way because there’s a ton of truth in what I’m saying here, in man-woman heterosexual couples.  But  if your gender identities are different from that in your couple, what I’m saying may still be very relevant and helpful, and I want you to see me looking you in the eye right now and saying I love you and support you and I’m not here to be heteronormative, just to speak from my experience and that of most of my clients.  Please feel free to message me with any questions you have about applying this guidance in your particular couple.

I want you to feel like you’re absolutely nailing it in as many parts of life as possible, including gift-giving, so you can thrive and have your love and your abundance bless everyone.  The world sure needs it, and you for sure deserve it!  So let’s dive in!

Why gift-giving in relationships can get so frustrating

First, we’ll want to look at the top two reasons holidays are so fraught with regard to men, in particular, giving gifts to their partners, and the places men sometimes go in the face of that pressure.  

Why are holidays so fraught for men trying to get their partner a gift? 

Reason #1: The Commercial Con-Job


Birthdays, anniversaries, Valentine’s Day, perhaps Christmas or another religio-cultural holiday… and for some, Mother’s Day… all can be land-mines in our material culture.  

Strong commercial interests, from Hallmark to DeBeers (diamonds) to the floral industry and beyond have flexed their persuasive muscles to convince women and our partners – especially in heterosexual unions – that love can and must be proven on this day through consumptive expression.

Reason #2: Pent-Up Desire 

Something also happens around holidays for women who’ve been self-sacrificial, patient, generous to a fault for the rest of the year.  Such a woman hasn’t ACTUALLY been entirely virtuous, though.  No, she’s been keeping a tab.  And now, fella, it’s time to PAY UP.  You can settle the score by getting this juuuuuust right.  But that’s a ton of pressure, right?

If you’re like many of my clients, here’s where you might go in the face of this pressure:

Option #1: Rebellion or defensiveness 

When you see how much pressure she’s putting you under, you might holler “no fair!” 

You might say, “I’m not going to play this game.”  

You might defend the things you’ve done for her or the things you’ve given her in the past and ask, “why wasn’t that good enough?”  

Option #2: Avoidance

Procrastination and forgetting are both manifestations of avoidance.  If you can’t win, if your chances of “getting it right” are paper-slim... why even go there?  

If rebellion is a deliberate ‘giving up,’ avoidance is a more subtle “it slipped my mind” or “Whoops!  Her birthday is tomorrow!”  So you actually direct your energy AWAY from the upcoming event, which further ensures disappointment and hurt all around.

Option #3: Throwing money at it

Some men try to make up in cash for what they haven’t invested in thought or time.  This sometimes works to an extent, because they pick something (e.g. jewelry, a car, beautiful clothes) that hits A spot, if not the HEART spot their woman was hoping for.  It’s hard to complain about carats worth of jewels or shiny new wheels, but they might not actually create intimacy and nourishment for you both.

None of these options get you to that successful, close, happy and hot connection you really want, do they?  

So let’s look at... 

The Easiest Way to Succeed at Gift-Giving and Experience-Giving in Seven Simple Steps:

Step 1.  Decide you want to hit a home run.  

Really decide that’s what’s going to happen this time.  If you make a clear decision, the resources for it to happen will come a lot more easily.


Step 2. Give yourself exponentially more time.  

Start planning - just small steps at a time - far in advance.  


Step 3.  Set aside an hour to schedule recurring reminders to yourself for the future. 

For example, a reminder to start thinking about holiday gifts in September or October each year.  A reminder about her birthday for 2 months in advance.  A reminder about Mother’s Day (if applicable - or just for YOUR mom!) for March.  An anniversary reminder for 2 months in advance.

BONUS tip:  include (even if you have to ask her what the dates were) the anniversaries of things like your first date, your first kiss, moving in together, your engagement, etc.

Step 4.  Make a secret note where you can keep a running list of ideas.  

When she shows you something in a magazine or “ooh”s over something in a store window, make a note.  Those are hints.

Step 5.  Get help.

Get to know some of her favorite stores, and pay one or more of them a visit with her.  Meet a salesperson she likes and say, “I want you to be my elf to help me get her great things here.  Will you please ask her the kinds of questions you know to ask and get the info you need to help me?”  Her friends and sister(s) are also key allies.

Step 6.  Use your words.  Write!  

Longhand writing is, sadly, becoming a lost art.  It will be SO meaningful if you will write to her.  

Simplest: write a note with three things you love about her, for the next event.  

More complex:  write her some of your favorite memories of the two of you.  Write her some of what you’ve learned from her.  

Longer-term: Start a little journal where you write something you love about her every day and give it to her a year from now.  

Step 7.  Outsource.  

Especially for milestone birthdays, call in other people who love her.  Plan a surprise party, or just a surprise collection of letters or cards.  Ask others to contribute; you’ll get the credit!

I trust those seven steps are helpful… but maybe you still want your partner to tell you what they’re desiring or what they prefer, yes?


Here’s how to teach someone to tell you what they want.  

First things first, we’ve got to get the person to believe that they can be thrilled to get what they ask for.  Many start out by requiring the giver to read their mind and give them what they want, without them having to name it.  

Many women seem to carry this belief that “if I have to tell you, it doesn’t count.”  But that belief really limits how much satisfaction we can get, since few partners - or few humans - are utterly clairvoyant mind-readers.  


Check it out.  Ask her, “do you feel like ‘if I have to tell you, it doesn’t count?’”  If she does feel that way, ask her if she’d be willing to reconsider that position, if you could assure her that in a few years, she won’t have to tell you anymore because you’ll have learned how to get her the just-right thing and do the just-right thing for her and with her.

Then, do these three things:  

  1. Ask her great questions like this one: 

    “Tell me about your deepest desires this holiday season? What feelings would my gift and my planning ideally evoke for you?”

  2. When you notice something she seems to envy someone else having or something she seems to really enjoy, ask

    “Is that something you might like as a gift?  What do you want me to know about that?”

  3. Tell her, “I’m learning how to really wow you with my gifts.  I would love anything you could provide to help educate me... Or if you’d rather I talk with one of your friends or sisters, let me know who, and I’ll do that.”

Now here’s a possibility I want to prepare you for: 

You may swing for the fence & miss.


There will be times when you put energy and creativity into a gift or an experience, and the recipient doesn’t like it, anyway.

In school or at work, you’ve probably gotten constructive feedback before.

Few accomplished people became accomplished by throwing in the towel when their ‘work product’ didn’t get rave reviews the first time.  We go back and edit and try again, right?  

We grow a thicker skin.  We develop resilience in the face of feedback.  It’s got to be the same in your relationship.  I know it’s hurtful in the moment, but this is for life.  She doesn’t mean to be critical of you; this is a sensitive area for her and her feeling really loved and seen and cherished by you is the goal you both share.  If her heart didn’t feel all that, you’ve got to wade back in there.

This is the point in the conversation with a client where they’ll often say to me, “But Michele, I really think it’s maybe IMPOSSIBLE to please her.”  Does it seem like your partner absolutely can’t be pleased?

Keeping with the school or work metaphor, if you had a professor or boss who just couldn’t be pleased, who was riding you mercilessly with a moving target, you’d probably quit or try to get reassigned.

At home, when we’re married, rather than seek another position, we sometimes just try to pretend that part of our role doesn’t exist.  But that’s really passive-aggressive and not fair to either of you.

What I recommend when it seems like she can’t be pleased is the same thing I recommend for when you know she can, but that you just haven’t hit on it yet:  DON’T STOP!  Keep evoking her heart’s desires from her.

An otherwise lovable woman whose satisfaction on holidays seems elusive is really pretty ouchy inside.  She’s got some yearnings and some old hurts that get in the way of her receiving what she really desires.  As her love, you are in a powerful position as a healer:  you can draw out of her what she really desires and you can help her heal the painful places where holidays still push her buttons.

Maybe you’re game for that… and then your next question is, “What should I say if I got her something that missed the spot?”  Here are a few of the best responses my clients have used, that their spouses responded well to:

  1. “I’m not here to defend my gift.  I’m here to get my satisfaction from totally delighting you.  I want you to partner with me to create those feelings for us both.  Are you willing?”

  2. “What feeling do you want your gift to evoke? What do you think would help you feel that way?”

  3. “Was it the essence or the particulars of the gift that didn’t give you what you desired?”

  4. (without any sarcasm or rhetorical-question vibe) “Are you willing to be met, seen, satisfied, and loved? If not, what part of you is holding back?  What would help that part of you?”

  5. If  all else fails, you can say, “I want to say something that’s painful for both of us.  I say it with deep compassion for where you are, and a commitment to helping you feel loved and seen and met by me (or whatever she’s said she wants to feel).  Are you ready?”  When she consents, say  “Your yearning might be bigger than this one holiday can meet.  How can you and I work on filling up your tank every day?”

There’s the crash course in how to hit a holiday home run… This holiday season, perhaps, and if not, then definitely over time.  This whole arena is one where a lot of pain gets buried and that means it’s a place where a lot of growth and healing and locked-away joy can be excavated.  

As you can see, my aim is not just an enthusiastic “thanks so much,  honey!” but a deepening of your relationship and a soul-level healing of the wounds of not-enoughness, unlovability, and frustration that shoot through most of the people I’ve ever met, no matter how high-functioning or basically happy we are.

Your full, enthusiastic, self-affirming, and patient engagement in this process has the power to help you feel not just successful with her (whew!), but to know yourself as a skillful and thoughtful lover and intimate partner.  Men who build this skill tell me they feel proud, self-expressed, loving, and powerful as a man, a partner, and a healer.  How cool is that?  It’s totally available to you, too.

So please, go use these tips now, and get going on your home-run holiday.  I wish you ease, fun, joy, and love, and I’d love to hear about it as you create it!