Valentine's Day at the office

How to avoid these common Valentine’s Day workplace dilemmas


Valentine’s Day is one of the biggest days, full of hope, best intentions and sometimes awkward moments. It wasn’t always this way. Remember the good old days in elementary school where the teacher assigned everyone to bring a Valentine’s Day card for every classmate? That way no one would feel left out. Then all of a sudden high school came and you started get notes and flowers from strangers but your crush was nowhere to be found. Or maybe you weren’t sure whether you should gift something so you either brought nothing or a big white bear with a red bow that someone had to carry around all day!

 Valentine's Day at the office

Now that we are all grownups, not much has changed, Valentine’s Day in the workplace can be just as awkward but that’s what I’m here to help you with. These are the top 5 scenarios you could find yourself in and I’ve given you a plan to come out feeling like a Valentine’s Day s-hero!


Scenario 1

Your partner is traveling for work and you won’t see he/she for Valentine’s Day

If your partner is away from home on a business trip, you still have several options to be present for Valentine’s Day. First, make sure your partner is into receiving gifts at work. If they are usually reserved or shy and you think there’s a possibility they wouldn’t enjoy it, then simply give them their gift at home upon their return.   Whatever you do, don’t take it personally. Couples crossing boundaries at work is one of biggest starts to a fight…..and there is NO fighting on V-Day-that’s Jen’ law! Enforce it!

So what to get them? Stay away from generic heart shaped chocolate or flowers. Go for something more unique and filled with thought –for example do you have an inside joke about mafia movies, cats or Jamaica? Give them something with a flair of that and their favorite chocolate. Want to keep it low key but intimate? Write a love note or send a picture in an envelope that you seal with a kiss and sneak it into their coat, briefcase or purse! Remember to spritz your perfume on it xoxo

Scenario 2

You have a crush or romance at work

Computer keyboard key - Be my Valentine

Valentine’s Day gives an “unspoken” pass for people to bring a gift to someone they may be romantically interested without putting themselves on the line. So don’t be surprised if your crush takes this opportunity to give you something. But let’s just say they are CLUELESS or you are keeping it under wraps, then you can take initiative and bring a little something.

Here’s the caveat, your best bet is to bring something for EVERYONE, like Valentine’s Day donuts, small candy bags or boxes. This way you don’t really single anyone out like in the awkward high school days. BUT you also get to hand deliver them to each person. See where I’m going with this?

Now you get to strike up a conversation with him or her. “The awesome weather today inspired me to be in he Valentine’s Day mood, here’s some candy I brought” which can lead to, “Any crazy Valentine’s Day plans?” –if none you can refer to Scenario 5.

If he has plans with Valentine’s Day already, iIt’s all good, better to know now, than later. If he doesn’t you could say, “Then you have to decide if 2016 is your year to find that amazing partner.” If the answer is YES this is my year, then you’ll say something like, “Me too, want to get some coffee or a bite to eat?” and if they decline better for you. You didn’t spend the night pining on that you “shoulda said” something.

Scenario 3

You receive a gift or flowers from someone you ARE NOT interested in or you don’t eat chocolate

Valentine's Day Candy and Roses

It takes cojones to go to someone you like and give them something special on V-Day. This person has been thinking about it for a day or two at least. Unless they ask you out on a date, this isn’t the time to turn them down. Don’t give things more meaning than is actually there. It’s just chocolate and flowers. Receive. Allow goodness in your life. If this person is being offensive in any way then definitely don’t accept and let someone know. Or if you have allergies just let them know too. If you don’t eat chocolate you could say, “Thanks, would you like to share it?” or just graciously accept and share it later.

Scenario 4

You just AREN’T looking forward to Valentine’s Day at work

You aren’t alone., a community where people share opinions about their workplaces, surveyed 1,000 employees and job seekers about Valentine’s Day. The survey results stated 58% of workers don’t look forward to the holiday. Maybe it’s time to change your view. Maybe get proactive this year and try something new for V-Day. A great team-building activity is put a LOVE & APPRECIATION BOARD, where everyone has access and people write on names of people and what they appreciate about them, they could do it anonymously. This could be up all week before Valentines. This not only lightens the atmosphere up but it builds a bond and camaraderie. Next thing you could try is a Secret Valentine, much like a Secret Santa. This way no one gets left out and it’s out of the box!

Scenario 5

You don’t have Valentine’s Day plans and not sure if you want some

MAKE PLANS anyway. Not sure where to go? Check out, they are NYC’s & the Tri-State areas go-to-site for all things dating, singles events and meeting someone special! In the event you change your mind or something better comes along you can always cancel. Even if you are waiting for a special someone to ask you out, makes plans on your own, at least you have taken care of yourself FIRST. Make sure you actively decide what to do. Most people end off feeling like crap because they thought something magical was going to happen AND it doesn’t. Don’t you think it’s time to create some magic for yourself! There will also be a variety of interest groups that night on getting together, so no excuses!


As always I am here for you and I’d love to hear what you have to say. Have you ever been in 1 of these scenarios? What did you do? Send your burning dating, love & relationship questions to I’ll be sure to answer you within 24 hours.

Our latest QUIZ, Find Out Your Dating Style has been said to be, “Exactly described how I’m dating and told me what I could do instead and what I was doing right.” Find out for yourself at