Memorable First Dates

By: Mike Cupolo and Tom Hollywood

You finally decided to text or did you call? Either way it worked. You got a response! He/she is interested in seeing you. Can you believe it? I can't. Not sure what they see in you. Nah, I'm just kidding. I'm sure you are a wonderful person that deserves nothing but the best. To be honest I'm surprised you managed to stay single this long.

You have a date. Awesome! Where do you take your date? Dinner and a movie? Boring. You want to do something exciting, a little romantic, and MEMORABLE! This is a monumental event. If he/she doesn't have a good time you probably won't hang out again. What if you are on a budget. I know I am. I wouldn't be writing this blog if I was rich. I wouldn't have a hard time meeting women either.

What is the best date idea? Where should you go? Tom and I thought of some activities that would make a fantastic first date. We also listed the cons of those fantastic activities. Enjoy!

Skydiving

PRO: The adrenaline rush and experience would make the date unforgettable.

CON: Very expensive and dangerous. Not to mention you have just paid to have a professional skydiver strap himself in behind your date.

    

Private plane tour of New York

PRO: Great scenery and very unlikely she's experienced it before.

CON: Still pricey and you’re probably getting into a plane with a guy who was a bigger fan of Jack Daniels then paying attention to where his 747 was going. He now gets to be your tour guide.

Amusement park

PRO: Roller coasters, food, games and the ability to get to know each other while on line. The levels of fear the rides induce will be perfect for discussion topics.

CON: Having to wait in an unfathomable line for a five second ride with your date can be rough, especially if the conversation isn’t flowing it can seem like an eternity. The group of twelve year olds behind your date making thrusting motions won’t help the situation.

   

Bicycle Ride around Governor's Island

PRO: Beautiful scenery devoid of cars and a great view of the city without the noise.

CON: Not for people out of shape. Nothing looks less manly/lady like then having a leisurely ride around the island and then getting winded going up a five degree incline. Sweating profusely is a side effect.

Minor or independent league baseball game

PRO: This is more of an intimate setting then a pro stadium. Increased fan involvement and entertainment between innings is an added benefit. Also cost friendly.

CON: Lets face it baseball is boring. What happens when the mascot starts to hit on your lady? Maybe you give him a playful shove. Then he shoves you back and next thing you know you are rolling around pummeling Jack the Jackal.

 

Musical Performance

PRO: Try to find a decent local band/singer that doesn't perform at a crowded bar or club. An acoustic performance at a place you can actually sit and talk between sets.

CON: Most of the singers are local for a reason and that reason is they are terrible. Expect the acoustic songwriter to be the overly sensitive type with long hair and just waiting to share his feelings. This will give you the urge to beat him with his guitar.    

Comedy Performance

PRO: There is always a quality stand-up, sketch and improv show every night in New York. Mike Cupolo's stand-up show for starters. He'll be funny. The jokes and close setting will spark conversation topics.

CON: He’s a bit of a bastard who likes to call out his friends when they come to a show. It’s going to be tough to convince her it was a different Tom Hollywood who dressed up like a fairy princess for Halloween.

Carnival/Fair/Boardwalk

PRO: The more local and less corporate the better. The lower budget will give you things to joke about, while the quaintness will give it that romantic vibe.

CON: Just can’t trust carnies.

    

Haunted House/Haunted Hay Ride

PRO: A Halloween date activity may seem childish, but with both parties already on edge it produces the needed adrenaline boost to make the night memorable.

CON: Some of the “pop outs” can be over the top and a little cheesy. Your date might not understand why someone in their mid twenties thought it was a good idea to go on a date to a place where the average age in attendance is single digits.

Skiing/Snowboarding

PRO: Even if both of you have no idea how, the fun of falling and learning something new is a can't miss.

CON: Its all fun and games until someone breaks their leg because they weren’t quite ready for that black diamond or doesn’t think getting hit in the face with a snowball was very funny. Not to mention you falling on your ass for the twentieth time as the ten year old girl zooms past you down the slope doesn’t look good.

Porn Convention

PRO: It is a porn convention.

CON: It is a porn convention.

BUT: Can’t think of a better way to figure someone out. It’s worth it to see the look on your date’s face. Probably looks similar to your face when you read this.

Apple/Pumpkin/Tomato/Anything you can go somewhere and pick it

PRO: Shows a sensitive side.

CON: Maybe too sensitive depending on what you’re picking.

Paddle Boats

PRO: An aquatic version of bike riding. This could be very romantic in the right setting.

CON: If your partner refuses to pedal it could be a long day. Throw in multiple paddle boats manned by kids and you are now involved in an unwanted game of bumper boats.

Beach

PRO: The pressure of approaching the opposite sex is over. Now you can enjoy the beach.

CON: You are a normal person and you are self conscious of your beach body. 

The Zoo

PRO: This shows you like animals and again brings out a sensitive side. Say you walk by the lion exhibit and see two lions going at it. That plants a seed in your mate’s subconscious that says, “I want to mate like lions.”

CON: Ok sure that is a long shot, but let me dream.