
Like it or not, Valentine’s Day is THE day devoted to love.
Although I like romance, I’m not fond of the day. It feels forced and commercial.
I don’t need the chocolate, greeting card and restaurant industry reminding me to express my love for Cosmo. We both do that every day.
But for some people – typically more so for women than men – celebrating Valentine’s Day in a big way is not optional . . . whether or not they’ve found true love.
If they’ll be alone on this big day, they’ll feel terrible about themselves, and may do foolish things, just to have a date . . . even with someone they don’t particularly like.
A little history and background on Valentine’s Day
Cosmo shared an infographic about Valentine’s Day that pulls together various data and statistics like these:
- Who started this romantic holiday and when? In 1537, England’s King Henry VII officially declared Feb. 14 the holiday of St. Valentine’s Day.
- Who started the tradition of a box of chocolates for Valentine’s Day? The chocolate box has been around for more than 150 years. The first Valentine’s Day box of chocolates was introduced by Richard Cadbury in 1868.
- How much chocolate is purchased for Valentine’s Day? Over $1 billion worth of chocolate is purchased for Valentine’s Day in the U.S.
- Who spends more on Valentine’s Day, men or women? Men spend twice as much on Valentine’s Day as women do.
- How many people propose to each other on Valentine’s Day? 220,000 is the average number of wedding proposals on Valentine’s Day each year.
- How many people do NOT celebrate this romantic holiday? 49% of adults DO NOT celebrate Valentine’s day. (If you’re not celebrating, this one Valentine’s Day fact will be a lot of consolation. You’re not alone!)
He suggests that, if you’re going out on a special date or to a party on this day of romance, you could sprinkle some of this Valentine’s Day trivia into your conversation.
Valentine’s Day Can Be Tricky in a New Relationship
For men and women over 60, in the early stages of dating someone, Valentine’s Day poses several problems or issues, impacted by how serious they are about each other:
- Is it too early in the relationship to celebrate the day?
- Or, should they plan a romantic date?
- Should they exchange gifts?
- If so, should they be meaningful gifts that express love?
- And how extravagant should the gifts be?
- Is a bouquet of roses for the woman obligatory?
- Is chocolate a must?
- Should you say “I love you” for the first time?
- Will having sex be in the mix?
It’s a lot of pressure . . . especially if you don’t know your potential partner very well and aren’t crystal clear about how they feel about you.
Should you just forget about dating on Valentine’s Day?
In the dating scene, some people are so averse to dealing with Valentine’s Day that they stop dating just before and after that date.
According to an article on Odyssey:
“Valentine’s Day makes people afraid to start dating someone. Dating gets put on hold for the few weeks before the 14th, because who wants to go on one date with someone only to have to decide right away whether to commit to a couples’ holiday together? Say “yes” to a Valentine’s Day date, and you seem too eager. But if you don’t mention the holiday at all, you look just plain out-of-touch.”
What about first dates on Valentine’s Day?

Let’s say you’ve had a few conversations, texts, emails or video dates with someone promising and you want your first in-person date with them to be on Valentine’s Day.
I always avoided it, even though my first dates were most often afternoon coffee dates, and not dinner.
Expectations on any first date are typically high. On Valentine’s Day, there’s even more pressure to have a romantic, good time on even established couples.
For those on a first date, it can be too much. Especially if you’re eating at a restaurant, surrounded by couples in love and showing it.
What if you want to do it anyway?
Everyone is different. You don’t have to do what I chose to do.
Maybe you can actually go into a Valentine’s Day first date with no expectations or preconceived notions, and just enjoy yourself.
My advice:
- Keep an open mind and keep your thoughts in the moment.
- Don’t think about a possible future with this person just yet. That can come later.
- Don’t put too much pressure on yourself and any potential partners by rushing things.
- Avoid having a Valentine’s Day date that’s memorable for being one of your worst dates. This can easily happen if your motive is to have a date . . . any date.
- Remember, it’s just one date so lighten up.
What kind of date should it be?
If you’re dating on Valentine’s Day, it’s wise to keep it simple. Make it a coffee date during the day. This is what I advise any first date should be.
What if you’ve had a few dates when Valentine’s Day rolls around?
How far do you go with things if you’ve only had, say, 3 or 4 dates in close succession with someone, but you have a very good feeling about things developing into a serious relationship?
If you misread the signals and go overboard, you could blow it before things have a chance to develop.
The wisest way to approach this is to discuss how you’ll deal with Valentine’s Day, even if you’ve only had one date.
You can be sure that she or he is aware of the day looming in front of you, too. So having a discussion about it should help de-stress things for both of you.
See how he or she feels about celebrating Valentine’s Day
If you put out feelers and she or he says something like, “Let’s not celebrate the day” or “Let’s not exchange gifts”, don’t fret. It could mean a number of things, not necessarily bad.
Maybe they really like you, but it’s so early in the game, they’re not sure how serious they feel. They don’t feel a gift or celebrating the day would be appropriate. Maybe they just don’t know how to handle it.
Or maybe they’re letting you know that they’re not that into you, and you can move on and find someone who’s a better fit for you. It may be a good time to know this, and you can both agree to end it.

Sure, you may have to deal with being alone this Valentine’s Day. But I think it’s always better to move on from a poor match early. Both of you are less likely to be hurt.
If you end up being alone, remind yourself that it’s a stupid holiday anyway.
How to celebrate Valentine’s Day when it’s early in the game
On the other hand, if things are working out between you, and you’re about to have the discussion, here are some tips on dealing with things:
A nice card alone may be most appropriate.
If it’s really early in the game – you’ve only seen each other a few times, over the space of several weeks or longer – any gift at all may be too much. A card should be just right . . . not overpowering, but showing interest. I wouldn’t go with a particularly mushy card, but something that says you like them. Write a few words of your own, but keep the word “love” out of it.
Don’t be overanxious to have a date – any date – on Valentine’s Day.
If you’re pushing too hard to avoid being single on this most romantic of days, you’re probably making too much of the day. It’s just one day. I don’t know about you, but when I was dating, I was much happier being alone on that day, than spending it with some near-stranger who didn’t mean very much to me.
Set parameters on how much you’ll invest in gifts for each other.
If you’re sure it feels right to exchange gifts, keep your investments reasonable. On my first Valentine’s Day with Cosmo we had been together for 3 months. And although we knew we had found true love, we set a $20 limit on gifts. It wasn’t really about the gifts.
A small box of fine chocolates or some kind of special candy would be appropriate. An interesting option would be a gift box of ingredients to cook a special meal together. Something meaningful to them, but not extravagant or intimate.
Going out for a romantic dinner may be too much.

Think how awkward this will be, if you’re newly together and you’re feeling it for her or him, but she/he isn’t feeling it for you. Why put yourself through such agony, seeing other couples clearly in love, but there the two of you are, anxious and waiting for dessert to be served so you can end the agony.
Even if you’ve been together and exclusive for months, you may want to avoid one of the biggest restaurant date nights in the year. Most will be crowded, over-priced and noisy. Not terribly conducive to love talk.
Consider dining in and making a special meal for each other.
If you’ve reached a point in the relationship where you’re comfortable going to each other’s homes, think about planning a nice at-home meal. It will be less stressful, and probably much more romantic than dining out. Cooking together can be lots of fun, and will reveal a lot about your partner’s temperament. Or, one of you can do all the cooking as a gift, like Cosmo did with me on our first Valentine’s Day together.
I love you. Love, love me do.
You’ve decided to go for a romantic dinner – either at home or at a restaurant. The atmosphere is romantic, with soft candlelight and music. You’re feeling in love with your date, and want to tell her/him so, but it’s only the third or fourth date, you’re not sure how they feel about you.
They’re giving you a look, but maybe it’s lust, not love. Should you dive in and say those three little words?
I’d say “No”. Don’t risk it. It may backfire on you. Once it’s out there, you can’t take it back. Wait until you’re really sure the feeling is reciprocated.
The most romantic day of the year doesn’t necessarily mean having sex.
Those of us over 60 (I sincerely hope!) are typically more cautious about speeding into intimacy than younger daters.
Of course, there are exceptions. Some throw caution to the wind. And what better excuse to take the plunge than Valentine’s Day.
My advice: If your relationship hasn’t reached the intimate stage yet and you previously discussed waiting a time before having sex, don’t feel pressured to have sex just because it’s Valentine’s Day. Stick with whatever timeline you’ve agreed upon.
More food for thought about finding love (on Valentine’s Day or any time of year)

Cosmo also wrote an article with some of the best true love quotes, including the following. Some are inspirational and thought-provoking, some are humorous:
People always say that, when you love someone, nothing in the world matters. But that’s not true, is it? You know, and I know, that when you love someone, everything in the world matters a little bit more. ― Jodi Picoult
True love gives us beauty, freshness, solidity, freedom, and peace. True love includes a feeling of deep joy that we are alive. If we don’t feel this way when we feel love, then it’s not true love. ― Thich Nhat Hanh
To say that one waits a lifetime for his soulmate to come around is a paradox. People eventually get sick of waiting, take a chance on someone, and by the art of commitment become soulmates, which takes a lifetime to perfect. ― Criss Jami
It is a curious thought, but it is only when you see people looking ridiculous that you realize just how much you love them. ― Agatha Christie
We’re all a little weird. And life is a little weird. And when we find someone whose weirdness is compatible with ours, we join up with them and fall into mutually satisfying weirdness—and call it love—true love.” ― Robert Fulghum
Alone or with someone, enjoy Valentine’s Day!
Whether Valentine’s Day finds you alone or with someone, I hope you have a happy one.
If you’re alone, along with dismissing the day as silly, spend some time loving yourself. It may sound corny, but reminding yourself of all the good things about you and all you have to offer is an important exercise to boost self-esteem and confidence.
It’s something to be done regularly . . . for you and for better dating. When you love yourself, you become a much more attractive potential partner to someone else.
If you do have a date with someone you like or deeply care about – no matter how you decide to celebrate – focus on each other and not the trappings of the day itself.
I hope my thoughts and advice have been helpful.
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More About Dating Over 60
Top 10 Best Online Dating Sites for Over 60: How To Choose and Use Them
5 Things That (Almost) Guarantee a Lasting, Healthy Relationship
10 Do’s and Don’ts If You’re New to Online Dating
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