How to prepare for the first date?

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Here we go—you’ve gotten the attention and you’ve picked the first date. Now it’s time to prepare for the first date. This is one of the only times you will have this much preparation unless you are going on more dates than a recently divorced 50-year-old. At the end of the day, you’re going to get the jitters. Getting ready for that first meeting can be much easier than it seems. Let’s break it down so you can walk into your date with confidence.

1. Dress with confidence (Be You)

Don’t ever be too scared to overdress. It’s important to be who you are. When you change your look, you now must rely on being fake for the rest of the date and even the rest of the relationship, as short as that will probably last. If athleisure is your thing. Do it. If it’s emo, do it. If it’s a leather jacket with a pooka-shelled necklace, do it. The goal is to feel comfortable and express your style. Let’s call it casual yet polished, but be you. A couple of bullets:

• Choose an outfit that fits the occasion. Whether it’s a casual coffee or a nice dinner, dress appropriately for the setting. There is nothing worse than someone who outdresses the other by 10 levels. There is a difference between confident and cocky. If they show up to a coffee shop right from a workout, perfect. That shows confidence and realness.

• Groom yourself well. A fresh shower, steamed clothes, and a bit of grooming (hair, skin, etc.) go a long way in boosting confidence. Do not forget the cologne (two sprays MAX). DO NOT be like Uncle Leo whose patchouli oil you can smell when he pulls up in the driveway.

2. Plan Ahead (But Stay Flexible)

If you're organizing the date, pick a spot that's relaxing and a good vibe. Classic first-date ideas like grabbing coffee, hitting up a local park, or going to a casual bar are perfect—less pressure, and more room to talk. We explained this in last week’s newsletter.

• Be sure about the location/time of your date but don’t be too early. It’s weird for you, the bartender, or bystanders watching you check your hair in the glass, bite your nails, or have the obvious nothing left to look at on your phone. If you plan it, pick a spot you feel most comfortable in. A little bit early is perfect.

Bonus: Have a backup plan in case things don't go as expected. Tip - know what you’re friends are doing so you don’t have to think of another idea. You can vet before you have to make the next move.

3. Prepare for Conversation

• Think of light conversation topics prior. The reason you’re reading this is because you’re not good at this so might as well prepare and do some research so any topic is doable. Script = NO but having a few ideas can prevent awkward silences.

• Ask open-ended questions. Encourage conversation by asking questions that go beyond “yes” or “no” answers. HINT: mirroring – whenever they say something for which you’d like to extend to avoid silence, repeat the last couple words of what they said as a question. We’ll explain mirroring in next weeks post.

4. Stay authentic

This may sound obvious, but the best way to enjoy the date is to just be yourself. Don’t stress about impressing your date—you're both there to get to know each other. Authenticity beats rehearsed or fake any day of the week.

Bonus: Take Care of Your Nerves

• Do something relaxing beforehand. Find your routine. Whether it’s listening to music, having a drink, or talking on the phone, doing something calming can help settle pre-date jitters. Also, if you’re nervous, acknowledge it. Be accountable for it. It will only make it less stressful.

• Remember: It’s just a date, not an interview. You’re getting to know someone new, and they’re getting to know you. Enjoy the process. If it doesn’t work out, at the very least you learned what to do and even more importantly what not to do next time.

Your first date doesn’t have to be perfect, but it should be you and most importantly, you need to learn. Remember, confidence is key. Tell me how it goes.

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.x

Yours Truly,