Dating Tips > Culture > The First Date Checklist to Help You Score a Second

The First Date Checklist to Help You Score a Second

First dates can be nerve-wracking. Even if you're excited, the anticipation for your first meet-and-greet is overwhelming. Take a breath, relax, and prepare for a good time. First and foremost, confirm how you see this date (potentially long term or just casual) and if it makes sense at this point in your life. Going into the experience knowing what you want out of it will help you filter your decisions.

Use the following checklist for before, during, and after your first date to help you score a second date (and a third… and a fourth)!

Take care of personal hygiene

Shower thoroughly. Shampoo and condition. Brush, floss, and pack mints. Moisturize your skin. Style your hair; apply light make-up; carry travel-size items for the mid-date touch up. Use deodorant. Trim or file your nails.

Pick an outfit

First impressions mean everything, and you don't want your outfit to ruin the night. You should look neat and polished. Dress for the environment (no suits at a coffee house). Wearing wrinkled clothes or stained jeans sends a message that you don't really care about being there. It takes seconds for your partner to decide what the future can hold - based solely on your appearance. A study from the UK showed women give a mere 90 seconds to decide if they want a second date (men offer a full 5 minutes).


  1. High heels elongate your legs and define your calf muscles. For the best effect, wear black heels with black hose or nude heels with a bare leg. Skip the ankle straps, because this will cause the opposite effect.
  2. Men should take extra time on their shoe choice. Women will judge this part of your outfit more harshly than anything else. Leave the running sneakers home unless the date involves a marathon.
  3. Don't wear anything you can't walk, eat, or breathe in! Comfort should be your priority. Look good to feel good. Avoid a new hairstyle or outfit idea, because it might make you self-conscious. Stick to the oldies but goodies.

Choose a location

Women care more than men about the nature of the date. The determining factors of acceptability include where it takes place and the effort put in. Your first meeting should never occur at a loud and crowded bar, because you won't be able to hear each other. Similarly, a movie should be saved for later. It removes the ability to converse and may even ramp up anxiety. The first date is all about bonding, so pick somewhere you can have fun and get to know each other.

Fun first dates ideas:

  1. Cooking class
  2. Paint 'n sip
  3. Bike riding
  4. Wine tasting
  5. Sports event
  6. People watching
  7. Zoo/aquarium visit
  8. Garden tour
  9. Bowling
  10. Boat/ferry ride

Prepare transportation

If you're picking your date up, clean your car, and fill your gas tank. If you're planning to drink alcohol, it's best to take a taxi or call an Uber. Add the taxi company's number in your phone or download a ridesharing app beforehand.

Bring money

Don't forget your wallet and bring enough cash to cover the whole tab. Whether or not the other person expects to go dutch on the date remains to be seen but expect to pay for everything. Whether it's drinks or dinner or one cup of coffee, don't chance the embarrassment of not being able to foot the entire bill… unless the other person is an adrenaline junkie who loves a dine-and-dash.

TIP: If the other person wants to half, say this time is on you. You can go 50/50 on the next date. (*wink, wink*)


Be yourself. Laugh at their jokes, but don't force it. When in doubt, smile. Lay off the heavy drinking, or you'll end up in dangerous territory. You need your wits sharp. Read into their body language to determine how interested they are.


  1. When someone subconsciously mirrors your body language, like yawning or smiling back, it means they feel connected.
  2. If your date moves closer or removes something that's between you (like a phone or a drink), it signifies trust.
  3. Eye contact is the universal sign of attraction. 
  4. The direction of your date's torso and extremities are a clear indication of how much they are enjoying themselves. If their legs face away, you're in trouble!


The most respectful thing you can do is put your phone away. Silence it if possible. Don't check your texts or your social media accounts if you feel awkward. It comes across as disinterest. A few moments of silence are okay.

Build momentum

Come to the date with a bunch of thought-provoking questions to maintain the banter. A conversation needs more than one-word answers to keep it going. This exchange allows you to relate and build momentum. It's best to end the date at its height (about one to two hours), so you're let wanting more. Finish on a high note, and you're on the way towards another date.

Ice-breaker questions:

  1. Who is the most important person in your life?
  2. What makes you laugh?
  3. Where did you grow up?
  4. What is your favorite thing to do on the weekends?
  5. What's the most interesting job you've ever held?
  6. Do you have a favorite vacation spot?
  7. What's the most embarrassing song on your playlist?
  8. What was the last book you read?
  9. Do you prefer early mornings or late nights?
  10. How would your friends describe you?


A skilled conversationalist listens as much as they talk. Communication is key. Think of it as a two-way street; you can't get to know the other person if you don't give them time to speak. The process of getting acquainted takes time. It happens when an equal exchange of information occurs between two individuals. As the relationship evolves, one partner may take the wheel… but you aren't there yet. Use the 1-for-1 rule where you ask a question every time you respond to one.


Usually, people tell you to lay it all out there - which is true for the most part - but too much too soon will backfire on you. Weighty topics should be avoided on the first date (for example, your ex). Yes, they will need to be addressed in the future, but heavy issues produce a false sense of intimacy. Venting and purging can make your date feel uncomfortable and you to seem immature and self-centered.

Be nice

Obviously, you should be nice to your potential partner, but you should also be mindful to how you treat those around you. Don't be rude to your server. Say "please" and "thank you" to hired help. Excuse yourself when squeezing pass others. Hold doors. Your date will view your attitude (or lack thereof) as a reflection of how you treat significant others in relationships.

Say goodbye

Here's the most important part of the date. It doesn't have to be embarrassing or complicated! The dynamic of this goodbye will set the future in motion, and one without physical contact may send the wrong message. Although all situations differ, it's best to hug or kiss (cheek is okay) when parting. Your date will perceive a wave as juvenile and a handshake as professional and stiff; they might also read disinterest in the lack of contact.

Rate the date

Just because a second date is possible doesn't mean it's necessary. Assess how you feel and rate the date on a scale from 1 to 10. Anyone who scores over 6 is worth another rendezvous. It's hard to know how far things will go after only one date but trust your gut. If the thought of seeing them again repulses you, don't bother hitting the next step. You already have your answer. And if you're not willing to invest your time, don't string the other person along.

Follow up

Initiate conversation afterwards. Don't wait for the other person to break the silence first. Send a quick text that night or the next morning to say you had a great time and would love to do it again. It's safest to wait for a response. A double text without acknowledgement can be construed as aggressive and clingy. Leave the ball in their court and move on if they aren't interested.

Kelly Martini, July 20, 2018

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