Valentine’s Day Tips and Warnings

Valentine’s Day is a tricky day, and it’s coming up. It’s a day celebrated as a holiday that is a bit of a big deal. There are arguments about the day. Some think it’s great and MUST be celebrated, and others believe that all of the mass-marketed and mass-manufactured Valentine’s Day “stuff” should be burned.

It’s also one of those days that I’ve never participated in as someone who is part of a couple.

I came close last year, but the guy I was dating was so out to lunch about how to be somebody’s boyfriend, or even about how to become somebody’s boyfriend that I probably didn’t expect much. He was good at sending meaningless texts though, substituting emojis for actual emotions, so there may have been a message with some emojis attached. I don’t remember though, and I deleted it. It wasn’t worth keeping.

My mom likes to celebrate most holidays, so at least when I was a kid I got to be her Valentine. A nice card and a little chocolate treat waiting for me in the kitchen in the morning on Valentine’s Day was a nice surprise. See MEN? I AM low-maintenance.

Sure, I’d like some attention, so a heart-shaped box of Smarties might not do the trick (and neither would a diamond necklace, incidentally). The man of my dreams is a little bit creative, and probably frugal. He’s waiting for the day after Valentine’s Day so he can get whatever is left at a discount, or maybe even a table at a nice restaurant. I’m even okay with the month after Valentine’s Day.

Word to the wise: don’t go into any drug store, florist, chocolate or candy store, or any place that sells mushy cards even if it’s to get food for your family on Valentine’s Day itself. This is especially true if you’re an introvert, or a person who can’t be bothered with crowds. There will be a lot of people milling about the stores not knowing what to buy (but knowing that they have to or ELSE), standing in lines and generally making the stores busier than they usually are when you go there to get important things like healthy food or medication. And let’s be honest, and rely on a stereotype here (and my own skills of observation): 95% of those people will be men in relationships with women. The women got their man’s gift on Boxing Day. Since I don’t like crowds or the way some people sometimes (mis)behave in crowds, I’ll be waiting until February 15th to get myself a Valentine’s Day present – hopefully there’s still some of the good chocolate left. Or maybe some candy hearts – those are pretty good too.

Want some other tips for Valentine’s Day? Here you go!


If you and your new squeeze said “no presents” for V Day, but you’re breaking that rule and you’re going to get your main squeeze something anyway, make sure it’s small and don’t act disappointed if they didn’t get you anything. You said no presents, remember?

If your person is an introvert and you got them an expensive and very pretty little something, don’t give it to them in a public place. Remember: introverts are usually trying to hide and avoid the spotlight. I’m an exception to that rule in some circumstances, but public gift giving can still be awkward. Sometimes facial expressions can’t be faked (that’s true in my case at least), so if I don’t like it, you’re going to know and so is everybody else.


I’m talking about marriage proposals. If you’re going to propose on V Day, go ahead, but definitely don’t do it at a professional Hockey Game if your fiancée-to-be is an introvert.  The problem is the “we don’t want a lot of attention” thing, and thousands of people could see it. Introverts find this kind of display of affection especially awkward. We don’t find silence awkward (in fact we’re glad when people stop talking), but we do find public marriage proposals awkward only because there are thousands of people watching in person, watching at home on their TVs (potentially), and watching on a big TV outside because they couldn’t get inside to see it. It’s so much pressure!

While proposing to someone on Valentine’s Day (or any other day) at a professional Hockey game is not such a good idea, taking your date/ main squeeze out to a pro Hockey (or whatever sport they like) game is a good idea (hint, hint; nudge, nudge future date/ boyfriend).

Valentine’s Day at Work

Oh boy, this could be awkward and could potentially involve a talk with the HR Manager at your workplace if you’re not careful. Valentine’s Day is not the day to “come out” to your secret crush who has no idea that you have a crush on them, or even who you are. You could create a situation where HR would have to get involved. It could also get very awkward very fast. I know it might seem like the perfect time to start sending “secret admirer” cards through the interoffice mail. Maybe you’ve been sending those cards already and dropping notes or gifts at the person’s workstation, and you’re planning a big reveal for V-Day, but once you reveal yourself, all 900 permanent, full-time, part-time, temporary, and contract employees from all shifts will know who you are and who you like. They might already know, and you just don’t know that they know: Yet. Just because it hasn’t been discussed by management at the latest Town Hall meeting doesn’t mean it isn’t news – it’s just not a metric with a target or “stretch-goal” attached to it.

And even in companies that tend to let the gossip mill run (not really a good thing), if HR is able to validate any of it, your news will make it into the next Town Hall meeting as a general warning about gossip and having too much fun on company time. They won’t mention your name, but you’ll know who they’re talking about and so will the rumour mill. After the meeting is over, they’ll all be having a laugh about it too. Good on you for making the workplace more fun! Also avoid letting anyone set you up at work. Talk about awkward; but that’s another story.

One way to keep yourself out of trouble, and still celebrate Valentine’s Day at work is to make it like elementary school. Your workplace may already be like elementary school anyway, so this could be quite easy. Here’s what you do: EVERYBODY gets a valentine card. Do you remember those cute little cards that had characters on them that everybody gave to everybody in Grade 2 or 3?  And you had to make sure you had enough for everybody, even the ones you didn’t like at all. I had a co-worker a few years ago who did just that – I think she had a lot of friends who were teachers. I thought it was nice.  It made me feel like a kid again, when I felt zero pressure to find a boyfriend.

Valentine’s Day for Single People

Valentine’s Day is not for Single People. It’s for lovers – or so “they” would have us believe. Last year I organized a “Galentine’s Day” party – no boys allowed! I know it sounds very exclusive, but there is nothing wrong with getting a bunch of girlfriends together over some appetizers and margaritas to celebrate having your bed all to yourself. Want to know more about being a single woman? Read “Single Girl Problems” by Andrea Bain. Being single is not a problem.

These are just a few of my thoughts, tips, and warnings about Valentine’s Day. Have you got a funny, possibly awkward yet inspiring story about Valentine’s Day?  Please share, I’d love to hear it!

2 thoughts on “Valentine’s Day Tips and Warnings

  1. Funny article Kathryn!! Happy Valentine’s Day any way!!! Hope you get some good left over chocolate!!

    Liked by 1 person

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