dr. jess valentine

Helping three Toronto couples decode Valentine’s Day

From a partner who won’t celebrate to a terrible gift giver and a lazy planner

Dr. JessJess O’Reilly is a sought-after speaker, author and sexologist (www.SexWithDrJess.com).


In my field, February is the busiest month of the year. Across North America, couples, community groups and even businesses prepare to celebrate all things related to love, relationships and sex. But for many, the buildup to Valentine’s Day is stressful, as the pressure to perform and celebrate mounts.

I’m not here to tell you what you should or shouldn’t do. You’re the ultimate expert in your own relationship, but I do have some insights and thoughts based on questions I’ve received from your neighbours in Toronto:

My partner refuses to celebrate Valentine’s Day. He says it’s a Hallmark holiday and won’t make any plans, buy any gifts or even get me (or the kids) a card. How do I get him to at least make an effort?

I’m in agreement that you don’t need to celebrate Valentine’s Day and that it is primarily a commercialized holiday. I believe you’ll gain more from investing in and celebrating your love each and every day rather than waiting for special occasions.

However, if celebrating is important to you and V-Day provides a reminder to do something thoughtful for your lover, I understand the frustration.

What if you let your lover know that it’s not necessarily about the date, but that you simply want to celebrate your love? Why not consider celebrating earlier or later in the week? Make dinner plans or send the kids to your parents so you can enjoy some alone time on the weekend. Be clear about what you want to feel (e.g., special, loved, appreciated, celebrated) and let him know how he can ensure you experience these emotions.

My girlfriend is the worst gift giver. Every year, I come up with something thoughtful to try to knock her socks off for her birthday and Valentine’s (they’re four days apart), and she just seems to grab some random gift online. Should I just keep smiling and pretending to like it or say something?

If she’s putting some thought into the gift but missing the mark, you definitely want to show some appreciation for her efforts.

On the other hand, if she really isn’t putting any effort into selecting something you’d like and receiving gifts makes you feel loved and appreciated, you certainly have the right to speak up. Since you put a great deal of thought into your gifts, you’re already leading by example, so you may want to bolster this with an explanation.

Let her know why you selected a specific gift and why you love receiving thoughtful gifts.

Of course, if you wait until you’re frustrated to express how you feel, you’ll likely find yourself complaining rather than making a request and she’ll be more likely to respond defensively. Plan ahead so that you can clearly convey what you want and why you want it. You may also want to lead her in the right direction, saying something such as “I’ve always loved opening gifts, and I’d love if you’d surprise me with something from one of my favourite shops. I’m sure they could even recommend something.”

Remember that you might naturally express your love by showering her with thoughtful gifts, whereas she might express her love via acts of service (e.g., making dinner) or carving out quality time to spend together (e.g. making fun weekend plans). While learning to speak your partner’s love language can enhance your connection, the fact that it doesn’t come naturally to her is not an indication that she doesn’t love you just as deeply as you love her.

Since we started dating three years ago, I’ve gotten into the habit of planning a big Valentine’s Day every year, and now my girlfriend has come to expect it. But I’m getting tired of doing all the planning (I do the same over the holidays and for our vacations), so how do I get her to step up?

Manage expectations and speak up. Your girlfriend has come to expect a grand gesture on Valentine’s Day, but you don’t have to fulfill every one of her needs or expectations. And you have every right to break tradition.

It’s not uncommon for one partner to fall into the planner role, and when you inevitably tire of it, you may find yourself feeling resentful. But no one is forcing you to do all the planning. Tell her that you’d love her to make the V-Day plans this year. You can let her know what you’re into but be sure to give her enough space to work her own magic. People who complain about planning often have trouble relinquishing control, so be prepared to take a step back and approach her plans with an open mind.