Here’s What Women Really Want For Valentine’s Day


Even in a committed relationship, Valentine’s Day can be stressful, but early in a new dating relationship, the whole specter of Valentine’s Day can be really, really uncomfortable.

A bunch of years ago, before the beau was on the scene, I dated a fella named Tim for a few months. He had kids and a dog, I had kids and a dog. I liked hiking and craft beer, he liked hiking and craft beer. Dating at middle-age is not easy, but all was going well and we were taking it slowly.

We had just started dating exclusively when Valentine’s Day loomed around the corner and was poised to create so many ways to feel insecure.

Will he want to get together on Valentine’s Day?

Is it weird to go out on Valentine’s Day when you are just starting to date?

Is it worth the hassle of getting a reservation and awkwardness of being around all of the lovey-dovey couples?

Should I pretend I don’t even know it is Valentine’s Day?

Instead of putting me through even a moment of insecurity, Tim took the lead. He said he hadn’t had a good Valentine’s Day in a long time and wanted to enjoy this one with me – and he asked me out for a special Valentine’s Day dinner.

He showed up wearing a spiffy suit, offering me a large bouquet of flowers and a lovely handmade card. He took me to a romantic restaurant, even though it was a weeknight and he knew I had to be home early for my kids. It was the best Valentine’s Day I had ever had. He made it fun, when it easily could have been awkward between us.

Seeing him solidly show up and take the lead was so attractive. He wasn’t hedging or holding back to see what I expected. He didn’t make a big deal out of Valentine’s Day because he had to or because he wanted to move the relationship along faster – he just wanted to do a nice thing for me. Even though our future together was undefined, he jumped in, took the pressure off, and made Valentine’s Day feel good for both of us.

He took the chance that I might ridicule or reject him – and seeing his confidence and generosity made me like him all the more.

This grand gesture made a big impression on me. Of course, it wasn’t a big enough impression to make me keep dating him when I found out that Tim was “technically” still married. That was a deal-breaker and quite disappointing, but the Valentine’s Day he gave me was a gift. He showed me the kind of partner I need to be with – someone who is brave and generous enough to be vulnerable. This experience made it really easy for me to spot this quality in the beau when I met him a few years later.

The willingness to put yourself forward, bravely and without expectation, is so important to creating intimacy. If you are willing to show up and make yourself a little vulnerable, it makes your partner feel safe enough to make herself a little vulnerable too, and, inch by inch, you get closer, feel safer, take risks being vulnerable, and build trust.

Men who play games and make women wonder where they stand are bound to find themselves in the unfulfilling, insecure relationships they probably deserve. In marriage or dating, women who experience this will end up backing away and protecting themselves. I suspect that these are the men who complain about never getting any lovin’ from their wives.

Men who take the lead and create a connected, transparent relationship environment where it is safe to feel intimate and attached, end up with women who love them passionately and find their foibles and idiosyncracies endearing, rather than infuriating.

Intimacy may be experienced differently by men and women, but both partners are responsible for creating a relationship safe-zone if they want to grow together. The hard part is that someone has to take the first risk being vulnerable.

Of course, intimacy is so much more complex than this post can encompass, but I firmly believe that growing together requires two people who are willing to show up and put themselves in danger of being hurt.

I hope your Valentine’s Day is filled with all of the dangerous, brave, and generous kindness you can handle.

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  1. Jean Owen says:

    Well Annie, once again you have used your words to describe an important quality in a relationship. I realize that, that is what David and I had. Lucky me !!

    1. annie kip says:

      I could tell that you and David had that kind of relationship! He was a very special man and he adored you, Jean. Even though this kind of connection is so tender and private, there is something magnetic about it. Couples who are this way with each other have a special ease together. I think we all want to be around that feeling – no wonder your house was always full of people!

  2. Steven Elder says:

    Best. Post. Evah!! I knew you were emotionally intelligent, but I didn’t realize just how smart until I read this. Fave line: “I firmly believe that growing together requires two people who are willing to show up and put themselves in danger of being hurt.” That spoke to me. That is intimacy. That is partnermates. And that approach is what makes for a relationship where everyday is Valentine’s Day. ❤️

    1. annie kip says:

      Thanks, so much, Steve! That “everyday is Valentine’s Day” is the feeling we all want in a relationship, right? It is so elusive and slippery to hold onto. For some reason, I think it is even harder in a marriage, which is counter-intuitive. You would think being in a stable relationship would make people more willing to be vulnerable, but it doesn’t always work that way – that would be a whole other post! Wishing you get back 100x the love and vulnerability you put out there, my friend!

  3. Deb White says:

    What a lovely article, Annie! I really enjoy your writing skills and the words you choose. Much love to you, my wonderful, beautiful, fulfilling friend!!


    1. annie kip says:

      You are so sweet, Deb – thank you. It is fulfilling to me to think through these thorny topics and write my thoughts out in a way that makes sense – at least to me. There is nothing quite a warming as hearing that a friend gets what I am saying! You are the best supporter, gal!

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