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Your First 5 Dates

Updated on March 19, 2011

Do you have a date? Congratulations. I’m jealous. Is it a first date? If so, here are some suggestions for men who are about to go out on a date with a certain woman for the first time. You want to impress her. You want to show her a good time. I’m about to give you those suggestions I mentioned earlier. I’m prepared to walk you through your first five dates. This information is free. Just remember, you might be the Mario of your Super World, but she is the princess and your only quest.

Date #1: Show up on time

Showing up on time is important for first impressions. If you show up late, that says her time isn’t as important as yours. If you do show up late, show up with flowers or a basketful of kittens, or at the very least, a fake speeding ticket, and then tell her how you got caught speeding, because you couldn’t wait to see her. Or just show up on time. Actually, get there half an hour early, so you can toss some rose petals on the path leading from her door to your car. And make sure to open the door for her. And clean out your car, beforehand. You don’t want that awkward moment when you have to tell her to wait while you clear away all the trash that’s on the floor and the passenger seat. Not unless it’s a bunch a kittens, then you can tell her that you picked them up on the side of the road on the way to her house, which is also a great excuse if you happen to be late. She’ll appreciate that you’re into helping animals. It doesn’t matter what you do on your first date, just pretend that she’s a painting and you’re the curator. It’s your job to make sure everyone else sees that she’s a masterpiece. Handle her with care and the utmost respect. Just remember, be 100% with your date. 10% you, 34% James Bond, 20% Jim Carrey, 16% Don Juan, and 20% woman. After the date, if you no longer have a use for the kittens, stick them in a stranger’s mailbox. This might seem cruel, but a mailbox will provide them shelter from the weather and predators, and mailboxes are usually checked at least once a day, so they won’t be in there long. But make sure the mailbox doesn’t belong to a Chinese restaurant.

Date #2: Cook her dinner

Is she coming to your place to eat? Pizza isn’t an option. Neither are kittens, so no Chinese takeout. Take a hint from Lady and the Tramp and cook up some spaghetti, but don’t share the same plate. Put on some music if you can’t hire an Italian guy to play the accordion. And buy some wine. Make sure you know everything about the wine, including what year it is and how to pronounce the name correctly. Don’t say the meal was easy to fix, but don’t say it was difficult, either. Say it was challenging. Say it has a secret ingredient, and then see if she can pinpoint what it is. When she gives up, tell her it’s love. You made it with love. Make sure the spaghetti is perfect, but also make sure to burn the garlic bread. This will say that you’re not perfect, even though you certainly try. Knocking over the wine bottle on the table and spilling wine on her dress is encouraged, but isn’t guaranteed to make it a perfect night. After you’re done feeding her dinner, you might want to feed her some poetry. Learning French is encouraged. You could read the obituaries to her in French and it’d still be romantic. After the date, walk her home and surprise her by pulling a guitar out of the bushes and singing her a song. Preferably in Spanish.

Date #3: Be selfless and generous

If you happen to take your date for a walk and you come across a puddle, take off your jacket and lay it across the puddle, so that she can walk over it. The same rules apply to oil stains, or manure, or homeless people who fall asleep on the sidewalk. If she says that her feet hurt in her high heels, then trade shoes with her. She’ll enjoy your Sneakers and you’ll get an idea what it’s like to be a woman. Don’t get too used to them, though, because high heels are addictive. If she’s cold, give her your jacket, but only if you haven’t previously used it to cover a puddle. If she wants something to eat from the hotdog stand, make sure to give the vendor a generous tip. One hotdog, $20 tip. Two hotdogs, $10 tip. Always carry cash on you, but never in an awkward place, like in your underwear. You don’t need to be digging in there in front of a hotdog vendor while you’re wearing high heels and a wet jacket. Keep the money in your wallet and keep your wallet in your back pocket, so it doesn’t look like you’re reaching for something else. Don’t watch her eat the hotdog. Purposely forget napkins, so that you can offer your sleeve to wipe her mouth. Also forget an umbrella on your walk. If it rains, your pure awesomeness will create a bubble around both of you, keeping you dry. After the date, pick an imaginary leaf out of her hair. Follow it up by brushing her hair over her left ear. Not all of her hair, like a comb over, but just a strand. Instead of turning and walking away, try back flips, instead. She’ll consider you her acrobatic gentleman.

Date #4: Show up on a horse

Imagine her surprise when you show up at her door on the back of a white stallion. A unicorn would be nice and would certainly make the night more magical, but don't get depressed if you can't find one. Ride bareback through the park or on the beach, if one is available. Take her to a secluded area, where you will have previously built a gazebo or carved one out of a single, giant block of wood. Turn the horse free, then enjoy a candlelit dinner inside of the gazebo. Make sure to serve exotic fruits or some sort of endangered species. Chilled monkey brains are encouraged, but hard to explain in an appetizing way. After the meal, take her to the hot air balloon that you will have rented for the night. Make sure the basket is lit up with dangling lights and that there’s a bottle of champagne on ice inside the basket, as well as two wine glasses. As the two of you soar above the city or the ocean, if one is available, propose a toast to the two of you. All you have to say is, “To us.” That says everything. Don’t say, “To tonight.” That implies that you only have an interest in her for that night, and not the many nights that you hope will follow. Don’t get distracted. Maintain eye contact. She’ll be impressed if you can’t stop looking at her, even though you’re hanging several hundred feet above the ground and a volcano just erupted in the distance. Keep staring into her eyes. Tell her she’s breathtaking. If she buys it, this would be a good time for that first kiss. Put a lot of passion into it, but not a lot of force. Be gentle, but strong. It should last exactly 4.23 seconds. Don’t immediately go in for a second landing. Wait for her to come 20 to 30 percent, and then meet her. And make sure to hold her if a second kiss actually occurs. After you finally bring the hot air balloon down, walk her back to her place and, if she’s willing and not airsick, go in for a third and final kiss. And then say goodnight.

Date #5: Be spontaneous and surprise her

Show up at her house at 4 in the morning and beat on her door. When she finally answers and sees the two suitcases you have beside you, tell her that you both have to leave right now. Be sure to stress the right now. If she asks why, tell her you’ll explain on the way. She’ll want more information, so add that it’s not safe for her to be there. Keep glancing over your shoulder. Your right shoulder, never the left. She’ll ask you where you’re going. Say someplace safe. She’ll be a little flustered, and she might say she needs to get dressed or pack something, but tell her there’s no time. Finally break down and let her get dressed, and then make your move. Open the two suitcases and release the iguanas that you have collected from various pet stores. Let them run into her house and then shut the door. Run away as fast as you can. There should be 14 iguanas in all, 7 to a suitcase, and each will be wearing a small sweater that you will have knitted for them, sweaters with letters on the back. The letters, when arranged correctly, will spell out a message. Rare WI Yummy LOL. If she manages to catch all the iguanas and line them up in the correct way, she can begin to decipher the message. Rare would be something that isn’t common. WI is the abbreviation for Wisconsin. Yummy is a description. The LOL is just so she’ll know that you think the whole thing is funny. Sure, you could just text her the message, but sending it by iguana is much more of a surprise and completely original. She’ll know that it’s something yummy and rare from Wisconsin. She’ll be thinking about what it could possibly be, and that’s when you show back up, several hours later at 7 o’clock. You’ll cook her breakfast, an omelet with a rare Bleu Mont cheddar from Wisconsin. If she doesn’t cringe at the idea, cook one of the iguanas, as well. But if all goes according to plan, she will be impressed and grateful for your attempt to surprise her. And she will be surprised, that’s a guarantee. There is the possibility that she might get the letters mixed up and misread your message, arranging the iguanas so that their sweaters say will you marry me. Oddly enough, that can also be found in that assortment of letters, but just cross your fingers and hope she ends up with rare WI yummy LOL, otherwise, she won’t be thinking about the meaning you had in mind. If you come back and she throws her arms around you, and says, “Yes!” then you’ll know that she screwed up your iguana puzzle. Either way, you’re enjoying a delicious breakfast or you’re getting married. But you’ll still have to do something with the iguanas, because she probably won’t want them in her house, anymore. A suggestion would be to put them in a mailbox. It might require up to 14 mailboxes, depending on the size of the iguanas in question. Or even less mailboxes, if you decide to cook one for breakfast.

After these first five dates, you’re on your own. Just try to make them interesting. If you need more advice, feel free to contact me. I can be reached by Bat Signal or by a message stitched onto the back of an iguana’s sweater. Or just leave a comment and I’ll get back to you as soon as I can. But remember, above all, just enjoy yourself and treat her like a princess, because all women deserve the utmost respect.

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