When you’re single, Valentine’s Day can be awkward. And if you’re in the beginning stages of dating, a dramatic gesture of romance probably seems more than just a little over the top. With that being said, your matches might have unspoken expectations: ladies might be put off if a guy they’re seeing doesn’t acknowledge the day or ask them to celebrate and guys may be surprised if their match doesn’t say yes to the plans offered.

To make it even more confusing, dating online often means you’re dating multiple people. And if you only send out one email at a time, waiting for a reply before you message someone else, you could be expecting the page to load with your click mate forever! Naturally, sending several messages also means receiving many replies, and sometimes, heading out on multiple dates in a week. Just keep in mind that anyone in your inbox who you have yet to meet offline shouldn’t receive a presumptuous “Happy Valentine’s Day” ping — stick with those you have an in-person connection with already.

But whether there are lots of potentials currently in the running for your heart, or just one, the way you handle the holiday has the potential to shift the relationship. Even if you just started seeing each other, your actions — or inactions — will be noticed, and may be telling to your match about where you two stand. So before you make any plans, know that the key to surviving the V-Day hype when you’re single is to keep things low key. Below are some casual options for handling the holiday.

1. Give Digital Recognition

Acknowledging Valentine’s Day with a text message or eCard is a great solution for a match you just met, or someone you’re still pretty casual with. Digital appreciation lets your match know that he or she is on your mind, and you appreciate them. Guys should do at least this with everyone they’ve met offline who they hope to date again. But ladies, hold off if you’ve only been on one date, guys may interpret this as aggressive rather than sweet.

2. Send a Woo-Worthy Treat

Good vibes can come in your physical mailbox, too. Whether it’s an Edible Arrangement® or something more personal your match mentioned on your last date, a special delivery says you care. Guys should do this if getting together on the 14th still seems too serious (for some fun ideas, check out my list of romantic gifts for women). And ladies can send a treat if he’s brought up V-Day already, but you couldn’t coordinate your schedules.

3. Plan a Night In

Forget dinner reservations — if you want to spend time with your match on Valentine’s Day, staying in is a better idea. Surrounding yourself with couples who are celebrating their Silver anniversaries at a swanky restaurant puts instant pressure on your relationship. Not only is a night in more low-key, but it’s intimate as well. So cook something steamy, pour a couple glasses of wine and enjoy each other’s company. If you’ve yet to spend time alone together at your place, it’s the perfect moment for more personal discussions… and a mega make-out session!

4. Create an Experience

Keeping things low-key means avoiding formalities (and formal attire), so think creatively if you’re planning a night out. Rather than sitting across from each other at a table, add movement to your evening. Get tickets to a concert, head to a wine tasting, or attend a food festival. Enjoying an experience together will create a memory that will have a stronger impact on your heart’s hard drive.

Remember — the less pressure that exists with your matches, the more likely your budding relationships will continue moving forward unaffected. It’s when you put too much pressure on your dynamic that you’ll get out of sync. Keep things simple and straightforward with a casual option that’ll still give you both the warm and fuzzies.


Laurie Davis is the author of “Love @ First Click: The Ultimate Guide to Online Dating” and the founder of eFlirt Expert. Her company has helped nearly a thousand singles navigate online dating by writing their profiles, tailoring messages for their matches, and managing their eDating lives. She was nominated for “Best Dating Coach” two years in a row by the iDate Awards. For more online dating advice, buy her new book.
  1. As Jews we’re not supposed to celebrate valentines day … It’s similar to Christmas … Best solution to the awkwardness is don’t acknowlegde it as a holiday at all !!

  2. Right, jews are not supposed to celebrate, but when I think of the 31’th of December, all I can think of is “Here’s the last day of the year. I should probably go out and meet the new years eve and be happy about it because new year is like a new beginning”
    Regarding Valentines, different idea, same thinking though..

  3. Assimilate, Jews!…and you can fret about what to do with no date on New Year’s Eve, or being single on Valentine’s Day.

  4. I kind of agree with the first comment first it is a Christian holiday as in St. valentine’s day. The only people who it was bad luck for was Bugsy Moran’s boys that fateful day in Chicago when they ran into the business end of a Tommy gun courtesy of Al Capone in the 20’s. Today it is now purely a commercial holiday and companies spend lots of money to make you feel less than if you don’t have someone or guilt you into spending on someone and making inappropriate and over the top gestures. Like anything the answer lies somewhere in the middle. First if alone like I am .. its another day. 2) If feeling sorry for yourself get out of your head and help another a relationship will not fix you. If in the beginning stages of a relationship some small gesture might be worth while. Finally, have a conversation with that other person and see what they think! Might be an opportunity to get to know the person better.

  5. As Jews there is never any harm in celebrating each other as a couple .. this my friends is always a blessing no matter what day of the month or year you choose. So leave the saints out of it and buy your girl some flowers, have some wine and relax already.. geez! I sure hope my fella reminds me that no matter what the calendar says, I am important to him and together we are blessed.

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