How to pick the first date?

Recommendations:

• Great watches: Bezel - $150 off your first watch w/ code NIKOSPEZIAL

• The most raw Dating Show you’ve ever seen: UpDATING

• Good read on psychology 

• The creator of newsletter platforms Big Desk Energy

• Thursday: Dating topics, meet-ups, and a dating app

As we move along the dating journey, we discussed “how to gain the attention of the opposite sex” and “how to make the first move”. Once you get the attention to make the first move, ask for the first date then get the acceptance, and you are ready to pick the first date. This is a crucial but significant step. It could be a make or break. Remember, even after speaking to this person upon first meeting or briefly getting a number, you still don’t know them. It is crucial to select something that is short, simple, and just as importantly, easy to get out of.

Selecting something short, simple, and easy to get out of allows you to go on a first date with expectations. Neither party knows what’s going to happen or who the other person is. Could it go well? Possibly. If you're confident? Still maybe, because you don’t know the other person. In one of my previous posts “The coffee date”, it explains why something like going for coffee is a great move. A coffee shop is public. It is usually meant to be quick. Most people love a coffee shop. It is acceptable to leave quickly. There is usually something for everyone (no need to worry about vegan, allergies, etc.). It’s cheap. If something happens, a coffee shop “grab & go”. Imagine asking someone on a first date. What is more appealing to one who you may not know and doesn’t know you: (1) would you like to go to a dinner where you’re stuck at a table god forbid something goes wrong or (2) would you like to grab a quick coffee?

Now let us break down the mindset:

The First Date Jitters

• The Hook: Planning the perfect first date doesn’t have to be nerve-wracking! Whether you’ve just matched online or have been flirting for weeks, making a good impression is key. Make sure the first date is fun, relaxed, and memorable. Be confident. The goal of the first date is not to have them fall in love but to have them wanting more.

• As you are planning the first date, make sure to set expectations low, and focus on having fun. Setting expectations low does not speak of your character. Ever hear the term “under promise, over deliver”?

Pick the Perfect Setting

• Tip: Choose a place that’s casual and comfortable. As I said above, short, simple, and easy.

  • Examples: Coffee shops, parks, public meet-ups, places with groups, casual restaurants, or bars. What else is a solid move? Meet someplace where they have friends and you have friends. This eases anxiety. They are already comfortable. They and you can have conversations, start conversations, set the tone by having others connect, and, most importantly, the ability to leave (this is not what you want to do but efficiency in dating is key)

  • Why: It keeps the pressure low and allows for easy conversation.

Next, Engage in an Activity:

• Tip: Make the date interactive.

  • Examples: topic at the venue you are currently at, something public, something where other people are having a good time around you, or do something such as how I met my wife, trivia night at Common Ground in NYC.

  • Why: Doing something active together helps break the ice and offers natural conversation starters. Also, based on psychology, when other people are having a good time, it naturally makes your mind think it wants to have a good time or laugh. Do you think people are actually laughing in the background on TV shows? Spoiler, they add laughing noises which naturally makes you laugh. Side note - go on youtube. Watch your favorite episodes with no laughs. It is not even close to as funny.

Anyway, back to where we were.

Plan for the Unexpected

• Tip: Always have a backup plan.

  • Examples: In case of bad weather, literally and figuratively, have a quick alternative. I’ve taken someone on a first date where I was early and my ex walked in. Additionally, flexibility shows you’re thoughtful and prepared.

Focus on Conversation, Not Performance

• Tip: Be genuinely curious about your date.

  • Examples: Ask open-ended questions about their interests, goals, and values, etc.

  • Why: Great first dates aren’t about perfection, but connection. Keep it light and engaging.

End on a Positive Note

• Tip: Gauge how the date is going, and be honest about your feelings.

  • Examples: If it’s going well, mention wanting to see them again. If you’re unsure, a polite and friendly goodbye is key.

  • Why: Being clear and respectful is important for both parties to avoid misunderstandings.

Bonus: First Date Don'ts

• Avoid heavy topics like politics or money.

• Don’t over-plan or put too much pressure on the date.

• Avoid distractions, like using your phone during the date.

Conclusion: Ready to Plan Your First Date?

Remember, the best first dates are about creating a comfortable space to get to know each other. Hopefully, with these tips, you’re all set to make your next first date an experience worth remembering.

Let me know if there is a topic you want to hear about, types of stories you want to hear, or anything you want to help you. Remember, everything is in confidence and with anonymity.

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Yours Truly,