Why I Love and Hate Valentine’s Day

Posted by in dating in midlife, love after 40, single women over 40 | 0 comments

Valentine’s Day: love it or hate it? If you’re single, it can be a challenging day. If you’re coupled, there’s so much pressure to do the right thing.

In preparation for Valentine’s Day, I was interviewed by Jim Jensen of the Essential Boomer Podcast. This was our third podcast together. You can also check out our first two episodes, episode 35: How to Have Great Sex at 50, 60, & Beyond and episode 24: How To Find Love After 50 – A Conversation With Sandy Weiner. Shows about dating and sex are super popular—who knew? Following are highlights of our latest show, where we talked about the love/hate relationship so many of us have with Valentine’s Day.

Why I Love and Hate Valentine’s Day!


Valentine’s day; you either love it or hate it. Why is it that so many of us have such a hard time with this holiday?

William Shakespeare said, “Expectation is the root of all heartache”. While Valentine’s Day can be wonderful, as it focuses your attention on your romantic partner, it can also put undue pressure on purchasing the perfect gift, making reservations at the most expensive restaurant, and buying just the right flowers. And if you’re single, Valentine’s Day can be a painful reminder that you don’t have someone special in your life.


I would think that the way we handle Valentine’s Day evolves as our relationships change. Couples just starting out face more unknowns and pressure than those of us who have been together for longer periods. What advice do you have for those just starting out as a dating couple?


I know someone who’s having her first date on Valentine’s Day! He’s traveling a few hours to her town, is staying overnight at an expensive hotel, and made reservations for dinner at an expensive restaurant. She’s a little uncomfortable with this over-the-top first encounter. It sets the bar really high for romantic expectation. Hopefully, they’ll be able to just enjoy each other’s company.

I recommend that you NOT schedule a first date on Valentine’s Day! But who knows, maybe they’ll hit if off, and it will be a great story to share with their grandkids some day. [*UPDATE: They definitely hit it off, and few months later, they got married! He still lives a few hours away until he can move his medical practice to her town, which will be this summer. Proving that with the right two people, obstacles can be overcome!]

If you are just starting out as a couple, keep Valentine’s Day simple. Focus on the true meaning of the day. And since you’re just getting to know each other, ask what would make your partner happy. Remember that small surprises, rather than huge gifts, can go a long way towards making someone feel special.

What advice do you have on how to keep the day special for long term couples?

Keep the romance alive by adding the element of surprise and excitement to your relationship.

How? Here are some ideas:

  • Hide love notes for one another.
  • Plan an exciting evening, and don’t tell him/her what the plan is. Build up the excitement and intrigue.
  • Go away together.
  • Have sex in a new place.
  • Go for a couples massage.

Some of us are all alone and have to deal with the media flooding us with Hallmark Holiday images of love and roses. This can be very depressing. What’s the best way to deal with Valentine’s Day if you’re all alone?

Valentine’s Day is not a reason for you to get depressed if you don’t have a romantic partner. This is a good time to fall even more madly in love with the most important person in your life – YOU. Take yourself out to that movie you’ve been wanting to see. Or throw a party for your single friends – a love fest. Watch a comedy, eat delicious food, and celebrate your amazing lives.

I am not a big fan of Valentine’s Day. It’s become a Hallmark holiday, designed to sell a ton of red roses and greeting cards, heart-shaped jewelry, and romantic movies.

Do you have any final advice for us boomers on how to make the most of Valentine’s Day and better yet, how to keep the romance going for the other 364 days of the year?

However you feel about February 14th, it’s always good to celebrate the love you have for your significant other or yourself. But why wait for this special day? Remember to pay attention to your own self-love every day. If you don’t love yourself, how can you expect your partner (or future partner) to love you?

And if there is someone special in your life, show them that you care in small ways every single day. That’s one of the best ways to keep your love alive. Create rituals (watching Netflix together every Tuesday, taking walks every night, special foods you love to cook together or eat out, your favorite restaurant for date night).

Remember that whether you’re single or partnered, it’s the small acts of kindness and caring that matter most. Be a giver of love. Giving from the heart fills you up with so much more love.


Listen to the episode here at the Essential Boomer!

How do you feel about Valentine’s Day? Please share your thoughts below.


Image: Flickr/Susanne Nilsson


Leave a Comment

Your email address will not be published. Required fields are marked *

AlphaOmega Captcha Classica  –  Enter Security Code

This site uses Akismet to reduce spam. Learn how your comment data is processed.