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How to Nail That First Date

first date tips

Unfortunately, we have all experienced that nightmare first date. She can’t stop talking about her ex or wait, is her father seriously at this dinner with us too? Either it was a firsthand experience or it was a story you’ve heard, but we are here today to avoid all of those first date horrors with some easy tips.

Ask a woman her ideal first date idea and it might start with he brings me flowers and end with a moonlit stroll through the park. We aren’t asking you to be Prince Charming by any means but there are some ways to wow her and have a great time yourself.

What To Wear

Depending on where you go for your date night, make sure you look the part. It’s all about first impressions here and the first thing she’s going to be looking at is you from head to toe. Dressing sharp enhances physical attraction and shows that you are respectful by nature.

You can never go wrong with a simple button down but whatever you do avoid those graphic tees and show your personality through conversation- not your shirt. We love this layered summer look with a lightweight jacket and plaid button down.


Lightweight Ludlow Sportcoat J.Crew $168.00


Draftsman Plaid Shirt, Jack Spade $168.00

We prefer dark wash slim rise denim over khakis that can sometimes give off a casual office feel which is the last thing we want to be reminded of on a date.


With your shoes, it’s always best to go with a nice pair of loafers or leather lace ups steer clear from flip flops and sneakers unless it is appropriate for the date activity.Kenton-Suede-Penny-Shoes

Kenton Suede Penny Loafers J.Crew $198.00

Where To Go

Choosing your date night destination can either be a major hit or a major flop. We have a fool proof destination to ensure your date night goes as smoothly as possible. To keep things casual and fun, we suggest steering away from a fancy restaurant with the intimate one on one feel that can sometimes feel more intimidating than inviting. Instead, we love the idea of going out for appetizers and drinks for a more laid back evening to get each other feeling more comfortable and relaxed around each other.


The Black Sheep in Jacksonville, FL is our ideal date night location. Their rooftop seating offers an amazing view of the city and an open fire pit to stay warm during chilly summer nights. The atmosphere and bar will keep both conversation and drinks flowing. Opt for locations similar to The Black Sheep near you that will provide that same atmosphere.

What To Order

For your first date together, it’s a little cliché ordering huge expensive entrees and expensive bottles of wine and you don’t want to blow all your money on her when you are just getting to know each other.  Instead, we suggest keeping things casual and sharing some appetizers together. Sharing appetizers allows you to experience more and gives a more intimate feel of sampling food together.

We still do recommend ordering a bottle of wine, however it’s important to order the right one. Be sure to impress her with Notorious Pink Rosé 2013, the perfect light wine both you and her will love. A sultry pale pink color, Notorious Pink exudes floral orange blossom aromas with citrus and red fruits and balances the juicy fruit flavors of ripe berries with zesty acidity and soft minerality.

Notorious Pink Rose Wine 2013

And The Rest Is Up To You

So there you have the ultimate first date fool proof plan. From your approachable style to the rooftop vibe, both you and your date are sure to enjoy yourself. She will be sure to appreciate a wine that is light and refreshing that you both can enjoy. Your date night will end with a great first impression that I’m sure will lead to more, but from here the rest is up to you. Have fun and enjoy yourself!

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