Man wearing a light grey suit holding flowers

The Gentleman’s Guide to A Killer First Date Follow these dating tips and you're sure to land a second one

So you’ve managed to convince that cute girl you met at the coffee shop that you’re worth her time and scored her number in the process. Great! Now all you have to do is convince her that you really are. When it comes to first dates, it seems like everything’s up in the air. Where do you take her, what do you wear, how early do you show up, how long do you wait to call her afterward… the list goes on. However, there are definitely some basic guidelines when it comes to dressing and carrying yourself that you should be mindful of. You want to do everything you can to land the second (and third, and fourth) date, right? That being said, here is our official list of first date tips so that potential second date in your future becomes a reality.

How to Dress to Land the Second Date:

First Date Tips to Land the Second - How to Dress

DO put some real thought into your outfit. According to, scientists say that men know whether or not there’s long-term potential for his partner within the first few minutes of meeting her, and the same goes for women. I don’t care if you normally wear jeans, t-shirts, and flip flops on a regular basis. On the first date, it is imperative that you dress yourself in a way that sends her a message that you take her (and her time) seriously, and that you put some thought into your time together. It only takes a few mere seconds for someone to form an impression of you. Before you even mutter “hello,” she’ll be sizing you up. Yes, that sounds intimidating, but it is a true statement of all of us. Appearance and first impressions are crucial. Even if you end up not working out after date #1, she won’t be able to look back on your evening together and make judgments about your lifestyle (slob living in his parents’ basement, most likely) based on your appearance, because you’re going to look damn good. Right? Right. And if you do end up working out, the good first impression you’ve made never hurts. It’s a win-win.

DON’T wear a suit. Unless you plan to take her to the opera and a Michelin-star restaurant (and hey, we’re not knocking that. If that’s the plan, go forth! Wear the suit.), don’t reach for that suit in your closet and think that it’s a safe choice. It’s not. Especially when it comes to the first date, you want to appear like you know how to dress yourself, of course, but you don’t want to come off as uptight. Save your suit for work and extremely special dates, and stick to more casual–yet still refined–separates.

DO wear a collared shirt or a nice sweater, or both. Make sure your clothing choices fit well, too. Stick to darker colors and neutrals for a classic look. Also, make sure everything is clean and pressed (so, do your planning in advance to avoid an embarrassing coffee stain situation).

First Date Tips to Land the Second - DO Wear a Collared Shirt
COOFANDY Men Casual V Neck Sweater Ribbed Knit Slim Fit Long Sleeve Pullover Top

COOFANDY Men Casual V Neck Sweater Ribbed Knit Slim Fit Long Sleeve Pullover Top

  • Soft Fabric 
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DON’T wear a tie. Unless the place you are taking her requires a tie as part of their dress code, feel free to skip the tie. Save it for the next date, after you’ve gotten to know each other, so your first impression isn’t “overly dressy.”

DO choose your accessories carefully. Stick to the classics. A nice watch, a leather belt, and good socks should do the trick without overdoing it. But, if you are doing the opera, we recommend going for the tie-pocket square-cufflink combination.

Soc Watch Belt 2
Black Carded Cotton Whittier Stripe Sock 239695 505 1280 0

Whittier Stripe Black Sock

A classic that will simply never go out of style, the Whittier Stripe Socks by Sock Genius are a definite essential.

DON’T overdo the cologne. I know you probably have that one signature scent of yours that you whip out for special occasions–which is great!–but keep it subtle. She’ll notice the scent (we promise) without you needing to pour copious amounts of it down your neck.

First Date Tips to Land the Second - DO Wear Amazing Shoes

Bruno Marc Men’s Leather Lined Dress Oxfords Shoes

Bruno Marc Mens Leather Lined Dress Oxfords Shoes
  • Classic lace-up design
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  • Flexible and comfort oxfords

DO wear amazing shoes (but not necessarily dress shoes, unless you’re going to that opera that we mentioned). What you’ll come to realize is that women are obsessed with shoes–both hers and yours. So, go for the cool boots, some nice chukkas, what have you. Your shoe game should be strong, because it will be one of the first things she notices, without a doubt. Casual shoes (boots, chukkas, nice sneakers) are fine for daytime dates, and for dates that take place after dark, reach for some lace-ups, loafers, or nice boots that don’t appear worn out. Keep the flip flops at home for the first date unless it’s at the beach.

DON’T do something new (i.e. that you’ve never attempted before in your life) with your hair! Don’t try a new hair style, and definitely don’t suddenly get a new haircut the day before. This could end in catastrophe, and must be avoided at all costs. Stick to your usual grooming routine. After all, why change up the hair that helped get you the date in the first place?

First Date Tips to Land the Second - DO Make Sure You're Well-Groomed

DO be well groomed and clean! You’d be surprised how quickly a woman will notice these things. Women are all about details. Make sure your nails are filed, your hair is clean, you’ve taken a shower, you’re wearing deodorant, and you’re cleanly shaven or “cleanly rugged.”

DON’T wear a baseball cap. Please. Unless you’re going to an actual baseball game, in which case, by all means.

First Date Tips to Land the Second - DO Wear a Jacket

DO wear a jacket, if appropriate. Layers are always good and at the end of the night, if she’s cold, you can offer her yours. Classy, gentlemanly, and it shows that you’re caring.

How to Act to Land the Second Date:

Your appearance is just 50% of the equation. The other 50% depends on you not only looking like a gentleman, but acting like one! A classy woman will appreciate a classy man.

DO arrive at the destination or at her house early. She will most likely be running late, but that doesn’t mean you should do the same!

DON’T berate her with questions, but…

DO ask her questions and hold a steady conversation. Women love to talk, and women especially love when you take a genuine interest in their lives, backgrounds, and aspirations. When talking, try to follow a 1-for-1 rule. When she asks you a question, take it as a silent cue that it’s appropriate to ask a similar question back after responding.

DON’T leave your phone volume on. In fact, try not to check your phone at all. Leave it in your pocket on silent and keep your attention focused on your time together.

DO be nice to everyone. She will notice if you’re rude to your waitress, or if you don’t clap at that opera or say “excuse me” when squeezing past people to reach your seat. Your attitude will be viewed as a reflection of the way you would potentially treat her, so be mindful.

DON’T let her go Dutch! At least not on the first date. If you were the one that asked her out, expect to pay for the date and grab the tab immediately as it arrives at your table. If she insists on paying, kindly decline or offer to go Dutch on the next date (Subtle, huh?). Feel free to go Dutch on all other dates afterward, but keep it old school on date #1 and wine and dine her to her heart’s content.

DO tell her that you had a great time, and initiate conversation after the date. It’s pretty hard to say which women believe in the “Two-Day Rule” and which think it’s bogus. A safe bet is to thank her for the date and tell her that you had fun either later that day, or first thing on the next day. Leave the ball in her court after that. You’ll have initiated conversation without being too forward, and it will be up to her after that to decide how soon is too soon to start discussing that second date.

And there you have it! Prepare your attire and your attitude in advance, and once the time of your date arrives, forget your worries and enjoy your time together. Knowing that you look good and are acting appropriately will give you the confidence you need to trust your gut and focus on the woman you’re with. She’ll appreciate your effort, and you can go forth and get to know one another in what should be an amazing evening (or day). Good luck, gentlemen!

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