100 Ways To Surprise Your Girlfriend This Valentine’s Day

Give her a box of nice chocolates and tell her that you can’t wait until tonight.

By Rob Gunther

Updated 8 months ago, May 9, 2024

In the days leading up to Valentine’s Day, try to act like you totally forgot about it. When she says something like, “So, what do you want to do this Friday?” make it like you have no idea what she’s talking about.
Then at midnight on Thursday, call her up and say, “Happy Valentine’s Day!” She’ll be so happy. Say something like, “I bet you thought I forgot about it, right?” When she admits that, yes, she did think you forgot, say, “Surprise!”
Try to catch her before she goes to school or work on Friday. Give her a single long-stemmed rose. Tell her, “Sorry babe, roses were so expensive this year, so I only got you one.” She’ll say something like, “Aw, honey, it’s OK, you know you don’t have to go crazy with the flowers.” Then call up a florist and have four or five dozen roses delivered to her office, or her first class, or wherever it is that she’s going. It’ll be a huge surprise, because she won’t be expecting it.
If she’s at work, try to sneak into the building. Pull the fire alarm. As everyone evacuates, hide behind one of the stairway doors and wait for her to walk through. Jump out at the last second and say, “Surprise!”
Give her a box of nice chocolates and tell her that you can’t wait until tonight.
Make sure you mix all of the chocolates up inside of the box, so that way she won’t be able to use the guide printed on the underside to figure out what’s inside each candy. That way each bite will be a real surprise.
While her whole office is outside waiting for the fire department to show up, ask her to point out the coworker who made that snarky comment about her scarf last week. Go up to that coworker and tell her that she’s wearing an ugly skirt.
Go into the bathroom and change into a suit. Walk into your girlfriend’s office and demand to speak to her boss. Pretend like you’re some higher-up from corporate, and insist that the company give your girlfriend a big raise, immediately.
Hang out in the hallway for another fifteen minutes or so. Wait for your girlfriend to settle back into her workday routine. Jump through the door and yell out, “Surprise!” again. It’s all about constant surprises. You want to keep her on her toes this Valentine’s Day.
Make a reservation at her favorite restaurant, but keep it a secret. When you go out for dinner, don’t tell her where you’re going. Have a taxi take you to one of her least favorite restaurants, and try to act all fake excited. Even though she’ll be bummed out, she’ll probably at least try to pretend to act really excited. Just before you walk in the door, tell her, “Just kidding!” and then take the cab to her favorite restaurant. She’ll be so surprised.
When you start eating, pretend you’re choking. When she starts to freak out, say something like, “Nah, I’m just kidding! Surprise!”
After dinner, it’s time to give her a Valentine’s Day present. It’s got to be in a small box, so she thinks it’s jewelry or something fancy. Then when she opens it, it’s just a Ring-Pop. You’ll share a laugh at the silliness of the gift, and while she’s catching her breath, that’s when you pull out another box. This time, it’s real jewelry. She’ll love it.
When the waiter comes around and says, “So, any dessert tonight?” make a face like you’re really full and say, “Baby, I think I’m too full.” She’ll say it’s OK. But when the waiter gives you the check, instead of putting in your credit card, give him a handwritten note that says, “Bring us some dessert. Make it a surprise.” And then when the dessert gets delivered, your girlfriend is going to be totally surprised.
After dessert, when the waiter drops off the real check, pretend like you left your wallet at home. When your girlfriend reaches for her purse, pull out your wallet and say, “Just kidding!”
When you give the waiter your credit card, give him another note, ask him to come back in a minute and say, “Sorry sir, your credit card was declined.” Act really embarrassed, and wait for your girlfriend to take out her wallet. Then let her in on the joke. Tell her it was all a setup. She’ll love your wacky sense of humor.
When the waiter comes back, give him your credit card, and give him another note. Tell him to come back and say, “Sir, I’m really sorry, but your credit card was actually declined this time, for real.” Pretend to be shocked. Get on the phone and pretend to call your credit card company. Say in a loud voice, “What do you mean my account has been terminated?” When your girlfriend tries to pay again, put down the phone, smile, and say, “Surprise! Just kidding!”
After you pay, give her a card. She’ll open it, and it’ll be a Christmas card. That’ll be funny because she’ll be expecting a Valentine’s Day card.
Wait for her to stop laughing, take the Christmas card away and give her another card. This one could be like a Halloween card or something. You get the joke, right?
Finally, give her a real Valentine’s Day card, but write it to a different person, and then sign it from a different person. That’ll be mildly surprising.
Now give her the same Valentine’s Day card, but this one with both of your names. But use superglue to seal the envelope shut.
Stuff the envelope with tons of glitter.
Go to a magic shop and buy those trick flowers that you can pull out from your sleeve. Pull them out and say, “Surprise!”
She’ll say something like, “I didn’t know you knew magic tricks!” Then you say, “That’s not all!” and now pull out one of those really long magician’s scarves from the other sleeve.
Also at the magic shop, get a bunch of those little smoke balls you can throw on the ground for a finale. At this point the whole restaurant should be applauding.
“Encore!” they’ll be cheering. Act like you don’t know any more magic tricks. But then segue seamlessly into a bunch of magician staples: card tricks, rabbit out of a hat, those three rings that magically link and unlink together.
As you leave the restaurant, drop even more of those smoke balls, this time grabbing your girlfriend and running out the door before the smoke clears. It’ll look like you both just disappeared. She’ll be totally surprised.
On the walk back to her apartment, she’ll probably say something like, “When did you learn all of those magic tricks?” Look at her with a confused face and say, “Magic tricks? What are you talking about?”
She’ll say something like, “Those magic tricks, back at the restaurant.” Scratch your head and say, “Baby, what are you talking about?”
She’ll be like, “Come on, knock it off.” Say to her, “Seriously, what’s going on? Is this a joke? I have no idea what you’re talking about.”
She won’t know how to react. She’ll probably say something like, “The magic tricks, from the restaurant, the smoke balls, the flowers out of your sleeve!” Stare at her and say, “Baby, are you all right?”
When she says, “Why are you doing this?” lean closer and say, “Sweetie, stand still. There’s something coming out of your ear.” Slowly reach toward the side of her face, and then pull out another bouquet of flowers from your sleeve. Say, “Surprise!”
If she continues to ask where you learned all of these magic tricks, just tell her that a magician never reveals his secrets.
As you continue walking back, tell her to hold on one second. Slowly get down on one knee. And then say, “I just have to tie my shoelace.” That’ll be pretty funny. She’ll definitely laugh.
When you get back to her place, see if she invites you upstairs. If she does, say something like, “I would, but I’m just really tired.” Give her a quick kiss on the cheek, and then start walking home.
Once she’s inside the front door of her building, race back around, climb up the fire escape, and sneak into her apartment from the bedroom window. When she unlocks the door, shout out, “Surprise!”
After she stops laughing, point at her chest and say, “Hey, I think you have something on your shirt.” When she looks down, bring your finger up and poke her in the nose, making a light, “boop!” sound effect.
When she stops laughing at that, ask her, “Hey baby, did you ever get my letter?” and when she says, “What letter?” say, “I guess I forgot to stamp it!” and then stomp on her foot. But just do it lightly, just for the joke, don’t really step on her foot too hard.
Ask her if she wants to go bowling.
When she says, “Isn’t it a little late?” tell her, “No, the bowling alley on top of the Port Authority is open all night.”
She’ll be like, “Are you serious? Or is this another one of your Valentine’s Day surprises?”
Tell her, “No, I’m serious, come on, let’s go bowling.”
She’ll be like, “I don’t know, it’s kind of late. And I’d have to get changed.”
Tell her, “No way, you don’t have to change, come on, you look great.”
She might really be beat, “I don’t know, can we just go bowling tomorrow?”
Grab her by the hand and say, “No way, let’s do it, it’ll be awesome, come on, we never do spontaneous stuff like this anymore.”
After she finally agrees, suggest walking, even though she’s tired and she’ll probably want to take a cab.
On the walk over to the Port Authority, a bunch of rough-looking guys will pop out of the shadows and surround you.
One of the guys is going to take out a knife and stab you in the gut while you collapse to the floor in a pool of your own blood.
The remaining thugs will slowly close in on your girlfriend. One of them is going to reach slowly into his pocket and pull something out.
It’s another one of those magician’s bouquets of flowers.
You get up off of the floor and say, “Ta-da!” It was a fake knife. Those guys were fake criminals. Your shirt’s covered in fake blood.
If she gets upset, just be like, “Come on baby, that was a surprise! Aren’t you glad I’m OK?”
When you get to the bowling alley, go for the whole, “I forgot my wallet” routine, just like you did back at the restaurant.
Surprise your girlfriend by buying her a brand new pair of really expensive bowling shoes.
Surprise your girlfriend by buying her a new bowling ball. It’s got to be one of those cool clear ones, with a glass rose or a heart inside. On the outside, make sure there’s a heartfelt engraving, like, “Happy Valentine’s Day baby, I love you.”
When you go to choose a ball, see if you can find a really light one, like a six-pounder. But act like it’s the heaviest thing you’ve ever carried. Struggle to lift it to your lane. And then when it’s your turn to bowl, just chuck that thing as hard as you can.
When you’re waiting for your ball to come back out of the ball return, stick your hand about halfway down the machine. Then scream out, “Ow!” and pull your arm back, but hide your hand inside your shirtsleeve, and say, “My hand! The ball return ripped my hand off!” Use some of the fake blood from the fake-stabbing before, if you have any extra.
Surprise your girlfriend by bowling a perfect three hundred. Yeah, it’s tough, but it’s not impossible. You’ve still got a couple of days to practice, so what are you doing wasting time on the Internet?
When you bowl a perfect game, be a gentleman and tell everyone that your girlfriend was the one who bowled twelve strikes in a row. Give her all the credit. When they enter her name on the bowling alley’s “wall of fame,” just give her a little wink.
Surprise your girlfriend by signing her up in a bowling league.
Get her a really nice bowling shirt with her name embroidered on the chest.
Pay for all of the bowling in advance, so that way she won’t feel bad about going every Tuesday night.
Offer to pay for her cab ride to the Port Authority each week, so she doesn’t have to take the subway.
After you’re done bowling, see if she wants to play Big Buck Hunter in the small video arcade next to the snack bar.
Tell her you’re going to get some change, but surprise your girlfriend by getting a bunch of snacks: pretzels, nachos with cheese, hot dogs, everything.
Also, make sure you get like fifty dollars worth of singles and put them all into the machine. “Look babe,” you can tell her, “now we can play every level!”
When you’re playing Big Buck Hunter, let her go for the easy ones closer to the screen. That is, unless she’s really good at video games. In that case, you don’t want to insult her by assuming she needs your help. Either way, when the golden bonus elk pops up halfway through the African safari tour, at least give her dibs before taking all of those sweet bonus points.
When you’re done playing Big Buck Hunter, surprise your girlfriend by saying, “But that’s not all the surprises I have for you.”
She’ll probably be super tired. She’ll say something like, “Come on, honey, I’ve had such a great time, but I’m so tired. Can’t we just go home and call it a night?” Surprise her with a couple Adderall.
The next surprise has to be really big, so see if you can charter one of those late-night helicopter tours around the city.
When you get to the helipad, surprise her by hopping into the pilot’s seat.
She’ll be like, “You know how to fly a helicopter?” Don’t even answer. Just take out your helicopter pilot’s license and tell her to buckle up.
Hire a team of fireworks people to start setting off awesome fireworks while you’re effortlessly zigzagging through the nighttime skyline.
Pull back from the cityscape just as the fireworks show enters its grand finale: “Baby, I love you. Will you marry me?” spelled out in fireworks across the sky.
Of course she’s going to say yes. It’s going to be the most romantic night of her life. You’ve seriously surprised her at every turn. But the surprises aren’t done yet. When she says, “Yes! Yes! Yes!” turn the helicopter around and start flying to Las Vegas. You’re going to get married tonight.
Surprise your fiancée by having all of your family and friends already out there in Las Vegas.
When you touch down at the Las Vegas helipad, surprise her by having a really famous designer fit her for a super expensive wedding dress.
When she walks down the aisle and meets you face-to-face, ask her, “Baby, are you surprised?” When confirms that she is indeed surprised, surprise her again by pulling out a giant jewelry box.
When she opens it up, she’s going to be really surprised, because it’s going to be just another Ring-Pop.
But that’s just a joke gift, just something to keep up the ever-heightening sense of being surprised. Pull out an even bigger jewelry box. This time it’s going to be a huge diamond ring.
After the ceremony, after you’re running down the aisle as newlyweds, surprise your wife by telling her you’ve got a tropical honeymoon planned, and that the plane leaves in fifteen minutes.
The Adderall might be wearing off here, so surprise her with some more as a quick pick-me-up.
Once you guys take off, tell your wife that you want to start having kids right away.
Tell her that you already have their names picked out, that you want to leave the city right away and cough up a down payment for a four-bedroom split-level ranch in Connecticut.
Surprise her on board the plane by bringing out a hairstylist. Insist that your new wife gets a really short haircut, so she’ll look more like a mom.
When she says, “But baby, we don’t even have any kids yet,” let her in on another surprise: that you already adopted three kids from overseas, that they’re already tucked into bed back at the split-level four-bedroom back in Connecticut.
“They’re already there?” she’ll say. “They’re asleep? Who’s watching them?”
Tell her that nobody’s watching the kids, which is why you’re going to have to cut the honeymoon short. “Surprise! The plane is actually on its way back to Connecticut right now. We should be there in a few hours.”
When you walk through the door of your new house, make sure there’s a really big dog wagging its tail to greet you. “Surprise! I also got us a dog.”
Also, get a cat.
Wait, maybe not a cat. Maybe get two dogs.
OK, two dogs and cat isn’t too much. I mean, you have a lot of space in that split-level ranch.
Also, a really big aquarium built into the side of the living room wall. Surprise your wife by telling her that all of the fish require different amount of food, and that the tank needs to be cleaned out once a week.
She might be a little overwhelmed by this point, but insist that she doesn’t have time. Tell her, “Listen, I’m sorry you’re having second thoughts, but maybe you should have thought about this before we got married. Now let’s talk about this later. Right now you need to get our kids to school.”
And she won’t even have met the kids yet. You’re going to want to time this perfectly. Have the kids run out and start screaming, “Mommy! Mommy! We’re hungry! We want breakfast!”
“Babe, don’t worry, I got this,” you’ll say as you surprise your wife by cooking the whole family a pancake breakfast.
Surprise your wife by taking her out to the garage to show her the minivan you bought for the family. Hand her the keys and tell her that the kids need to be at school in ten minutes.
When she goes to open the sliding side door for the kids, tell her, “Honey, wait,” and surprise her by showing off that it’s one of those hi-tech new minivans where the doors open by themselves by tapping the keys.
Give her a big kiss before she backs out of the driveway and say, “I love you baby, Happy Valentine’s Day.”
As the car disappears down the street, give yourself a pat on the back. You totally did it. You totally surprised your wife this Valentine’s Day. Now get inside and get some rest. That was a huge night that you just pulled off. A hundred intricate steps without any hiccups? That’s no tall order. Go take a few Ambien, because you’re probably all jazzed up from the excitement. Get some rest. You’ve set the bar pretty high, and it’s going to be hard to top all the surprises from last night. Happy Valentine’s Day everybody!