17 Crazy and Creative Ways to Ask for a Date

When I first ran across this handy guide by Barbara Seegmiller in a used bookstore a year ago, I fell in love with its kooky vintage greatness, for it is certainly creative and fun-loving and by following its rules you’ll definitely get…results. Published in 1986 with help from the English Department of Brigham Young University, it features a stern lecture from the then Associate Dean of BYU on the pitfalls of boredom in youth and boy does it deliver.

Packed with over 300 suggestions by the young in Seegmiller’s community on how to win over that special someone, CWtAfaD undulates wildly between the endearingly corny bad puns/clean cut fun of the ‘80s (i.e. “Give the person a pillow and with a note that says ‘Jane, I’d like you to go to the ___ with me. SLEEP ON IT, and then let me know!’”) and the clinically insane. Yes, this book has advice straight out of the D.E.N.N.I.S. system, suggestions that would be deliciously criminal outside the hearts and minds of the innocent 80s youth, including dragging up a mysterious wrecked car to sit on your crush’s lawn just to tell them you’ll be a WRECK if they don’t go out with you (the punch lines are all in caps, indicating that you must shout this at them). It’s so subtly creepy and wonderful that it’s presented as bona fide advice that it just can’t be left untold. So without further delay, I present to you 17 of my personal favorite crazypants suggestion from Seegmiller’s wonderful pages.


Attach a PEST CONTROL sign to the side of a van, dress as an exterminator in white clothing and ask several friends to join you. With the van parked at the person’s home, so the sign can be read, have all your friends lie on the lawn as if dead. With sprayer in hand, ring the doorbell and say: “I got rid of all the PESTS who wanted to ask you to the Prom so I could take myself! I hope you don’t mind!”


Have at least five of your friends who own cars form a half circle with their carl lights shining on the sign that has been placed on the front lawn of the person you are asking out. Everyone should put their radio or stereo on full blast. When the person being asked opens the door they will see a sign which reads: “Julie, wave if you can attend the _____ with ____ Saturday night. If you are busy, it is OK. Just say, ‘Good night.’”

– Nothing gets a girl all hot and bothered like polite conditionals.

3. VOMIT (the fake kind at the variety store)

“I would be SICK if you couldn’t attend the ____ with me Friday.”

– This one was circled by the book’s previous owner.


Have two large guys, dressed as paramedics, charge into class, business, home or wherever. A loud ambulance siren (on tape) is blaring as they enthusiastically find the PATIENT (who is suffering from exhaustion and going hysterical at the moment). They grab him/her securely, put him/her in a straight jacket and then on a stretcher, and take them to the person who is inviting them out. Don’t let the person off the stretcher or out of the straight jacket until they say yes. Sure hope they like you!

– This one had me confused. At first it seems like the “patient” would be the object of affection, but then it says “who is suffering from exhaustion and going hysterical at the moment” which makes me think it’s a friend helping out, a very good friend who will let you tie them up in a straight jacket and be restrained by two “large” guys (I love the attention to detail here, so quietly sinister). But it must be the o.o.a., for he/she is clearly being held hostage in a straight jacket until she agrees to the date. This one has it all: physical intimidation, coercion, mind tricks, and humiliation. Seegmiller, you are an evil mastermind.


Instead of toilet-papering a yard, STRING it: “a. Hope you are no TIED UP on Friday…” “b. STRING along with me and we’ll…”

– The good thing about string is that, unlike toilet paper, if it rains it won’t come apart when your crush has finished picking string out of her parents’ thorny shrubs after she gets done filing the police report for vandalism.

Brad Pitt used this same tactic to whoo Angelina.


Arrange a fake situation where guys are making the girl you want to take out feel uncomfortable. Walk up, observe and get rid of the hecklers. You may even wish to pretend you are punching your friends’ lights out.

– Seegmiller clearly hasn’t seen Mr. Deeds.


Fill a new trash can with empty cereal boxes, washed out tuna and vegetable cans, empty milk and egg cartons, papers and anything clean that would be a good filler. Tape a message to the inside bottom of the trash can: “I think it is a BUNCH OF GARBAGE having to do dumb things like this to ask for a date!”

– So romantic.


Get permission to dress up and be a MANNEQUIN in a window. Have the person’s parent or friend take them window shopping and just happen to walk by your window. They should stop and admire the display until it is determined that one of the mannequins is alive. A sign could finally be displayed through a window to ask the question. I dare you!


Dress in your KARATE outfit and then confront the person you are asking as if you are going to attack them. “If you don’t go to the ___ I’ll____ you.”

– I for one am hoping that the first blank is Morp and the second blank is scissor kick. Fun fact, this is how my dad first met my mom.


Rent or borrow a ROBOT. Have it follow the person around work or school, tactfully making comments that are about or to the person you want to ask out. The ROBOT pictured has just placed an order at the Artic Circle: “Hello, I would like one Bounty Bacon Cheese, a large order of fries, one chocolate shake and ONE DATE TO THE PROM. Does that COMPUTE?”

Remember, this was back in the 80s when everyone had a sentient robot (or robot child) lying around in their garage.

I was gonna snark on this more or make a Romney joke but there’s a real life picture of a robot hitting on the ladies and I think that’s pretty damn awesome.

11. TENT

Kidnap the person from school, home, or work.  Drive them around for quite a while and then escort them into a tent and seat them. You now shut the tent and remove the blindfold. To their surprise, they are among friends, seated around a fun candlelight dinner. The joke of the whole thing is that you are doing all of this in THEIR back yard. You can have them find the invitation to the ____ inside their food, written on top of the tent, across Joe’s forehead or whatever.

– Yes, your date is sure to appreciate being kidnapped from work and driven around aimlessly, especially when she sees the GO OUT WITH ME? frantically scrawled across Joe’s forehead in what looks like dark red ink. I especially like the clarified detail “To their surprise,” indicating that whoever came up with this idea knew the kidnappee would likely be sick with fear and prepared for death and torture. The only thing this one is missing is a jawbreaker. The best part is, this is one of several kidnapping suggestions—see the cover picture.


Get permission to pitch a tent on their front lawn. Make a pretend fire, set some rocks around the fire, hang some clothing around, have your sleeping bag in the tent and do whatever you must to make the camp look well lived in. Be in camp when they return home or get up. Invite your new camping partner for stew and then ask them out. If you do no intent to take no for an answer, say you will be living there until…

– Her body stance really says it all.


Have someone help you put the person’s car on blocks. Not too high, because you want the person to get into the car and not be able to leave before they notice. When they get out of the car and look under, they see your note: “Hi! Now that I have your attention, how would you like to attend the ____ with me?”

– This is my favorite suggestion. The only thing that could make it more majestic is the stern “Would Not Give Name” written right underneath it.

14. BEES

A small container of bees:

a.       HONEY BEE my date to the  ____

b.      May I BUZZ over and take you to the ___?

c.       If you can’t go to the ____ I suppose I’ll have to BUZZ OFF!


Place (or have someone in their family do it) an alarm clock under the person’s bed and have it set to go off at 3:00 a.m. When the alarm rings and the person wakes up, it will take a while for them to find the source of the noise and your note: “Don’t be ALARMED. It’s just me wanting to know if you can go to the movie tomorrow night?”

– …….


Carefully lower yourself upside down in front of their window, holding your message: a. “Thought I’d DROP by and ask you to the….” b. “I thought I’d HANG AROUND and ask you to go bowling tonight.”

Sheena respected the privacy of the bedroom. She chose the bathroom instead.


Deliver a large pumpkin with a knife stuck into it where the lid will be cut. The knife should also pass through a note which says, “To find a special message, you must remove the insides.”

The note inside (a slit should be made in the bottom of the pumpkin and a plastic-wrapped note inserted) states your request. They could be asked to carve a face and put the pumpkin on your step with a candle in it, if they can go. A smiling or frowning face would also relay their message.

– This last one is specially dedicated to commenter BlanketDenial and the late Jack Handy.

Puns, man. Chicks love puns.

If you have any delightfully unnerving dating solicitations or suggestions on par with Ms. Seegmiller please share them. If you decide to follow the advice here, please reach out and be sure to ask permission from your intended’s parents/obtain a warrant/know that you will likely be questioned by authorities and possibly detained. Go forth and woo!

“Creative Ways to Ask for a Date” by Barbara Seegmiller is available on Amazon.

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