How To: Ace The First Date

Alright, gentlemen,

I know some of these will probably be painfully simple – but you’d be surprised how often they go overlooked.

You had what it takes to score yourself a first date, now make sure you do what it takes for a second one.

As crazy as some of this might sound, some of this article is inspired by actual stories from actual girls who had actual experiences. Here goes…

  • Do – Guys, pick her up. 
  • Don’t – Make her meet you at your destination.

Put in the extra effort, don’t make her take a cab or take her own car. Some women may not feel comfortable with you knowing where they live before they get to know you, so if she insists, agree on meeting.

Bonus: Are you really into her? Use the Uber app on your phone to send a black car to pick her up. It’s a classy move and I can almost guarantee nobody she’s gone out with has ever done it before. Use this link to get $20 off of your first ride.

Why Jealousy Will Ruin Your Relationship

  • Do – Dress appropriately for the occasion.
  • Don’t – Dress like you’re going to the gym or sitting around the house. (C’mon man).

Chances are, the woman you’re taking out is going to put some serious effort into how she looks (make sure you notice and compliment her). Show her the respect of doing the same. Plus, when you look better, you feel better. And when you feel better, you do better in all areas of life.

  • Do – Open the car door for her.
  • Don’t – Watch her stand there waiting for you to open it while you go around your side.

Chivalry never goes out of style. The small things speak volumes, and you will be surprised when she tells you how “nobody does that these days.”


  • Do – Feel free to order a couple of drinks (or a few, depending on your tolerance).
  • Don’t – Go overboard and get sloppy. And definitely don’t show up already drunk.

This should be obvious. Know your limits.

  • Do – Be polite to the waiter/waitress/anyone you meet.
  • Don’t – Be impatient or rude, any ‘nice person’ who isn’t nice to the waiter, is not a nice person.

There is absolutely no reason whatsoever to be rude to anyone. Keep calm and be polite, simple mistakes aren’t that serious, and are certainly not ruining a night over. Steak undercooked? Great – more time to get to know your date while they correct the error.

  • Do – Keep the conversation light and casual. Find out each other’s interests, but it’s not an interview or a plan for the future.
  • Don’t – Talk about how beautiful your kids are going to be.

Too much too soon, man – trying to name your kids on the first date is a great way to make sure there isn’t a second date.

  • Do – Show up on time.
  • Don’t – Keep him or her waiting, you only get one first impression.

Common courtesy and respect needs no explanation.

  • Do – Keep your phone in your pocket.
  • Don’t – Make your date feel like your Facebook or email is more important than they are.

As common as it is that everyone is on their phone these days, have the manners to ignore it when you’re on a date. Just do what the rest of us do and check it when you go to the restroom, or when she does.


  • Do – Pick up the tab, guys.
  • Do – Offer to split it, girls.

A first date should absolutely under no circumstances have the bill split. Unless of course, that’s where you want the relationship to end. Don’t take a woman somewhere you can’t afford to pay for.

  • Don’t – Accept the offer, guys (seriously).
  • Don’t – Agree to a 2nd date if he accepts the offer, girls.

A respectful woman will offer to pay half, and will most likely reach for her wallet. This is out of courtesy and should never be taken seriously by a man. Show her appreciation that she made the gesture, but that’s as far as it goes.

  • Do – Tell the truth.
  • Don’t – Exaggerate to get them interested in you.

Dishonesty is a recipe for disaster right off the bat. If you’re out with someone who you genuinely are interested in a potential long term relationship with, eventually they’re going to find out if you’re lying to them or “embellishing,” and it would end up worse than if you were honest in the first place. Just be you.

  • Do – Ask genuine questions and attempt to learn about the other person.
  • Don’t – Make it all about you.

You have two ears and one mouth for a reason – listen twice as much as you speak. “What’s your favorite movie?” is not a question to ask someone you’re truly trying to get to know. Be genuine and show your interest. Find out her passions, her dreams, her ambitions. What makes her get up in the morning?

  • Do – Go for the kiss.
  • Don’t – Wimp out.

Going for the kiss on the first date will show your intentions clearly off the bat and will leave no room for question or insecurity if nobody makes a move. Guys, it will also keep you out of the dreaded friend zone. If she’s interested and kisses back, you’re in, because friends don’t kiss. If she’s not and she just goes for a hug, you know where you stand, early on.


Your first date is your only real opportunity to gain this person’s interest, but make sure you’re genuine about it. We all put our best foot forward to make a good impression, but don’t send your ‘representative’ who isn’t really what you’re all about.

And really, have some common sense. Be a gentleman (or a lady), Respect boundaries. Don’t be clingy. Don’t be weird. Don’t make him/her feel uncomfortable. It really is that easy!

Let me know how date two goes.

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18 thoughts on “How To: Ace The First Date

  1. As a painfully shy woman, I definitely appreciate subtle physical contact to get me used to someone in my space. If I spontaneously grab his hand when we’re crossing the street or walking somewhere take that as a sign that I wouldn’t say no to a kiss at the end of the date.

    Clear intentions makes it easer for us wallflowers to enjoy our date’s company without obsessing over the will his kiss me/won’t he kiss me butterflies.

  2. I do not like this idea of women not paying for their share of the meal. I feel paying for my half of the meal is a strong sign of independence and if my date and I were going to eat out, ideally, it should be a place I can afford so that I may pay for my own meal. That means, it is a discussion between the couple rather than a decision made by the man or woman alone. Women earn as much as, if not more than men in many equal opportunity professions.

    I wonder why a woman would feel insulted if a man does not offer to pay for her share; as I would feel a bit offended should he insist to pay for mine. In Scandinavian countries, women and men pay for their respective halves of the bill every time they go out. Women’s stand for equal rights is very strong there. It is the same in Australia.

    I think keeping true to a person’s word is a strong sign of a gentleman, more so than sticking out a few bills to pay for a meal. And ladies can be ladies while paying for their meals too. In this sense, I mean having a strong sense of confidence in being female and belonging in an equal rights world; yet enjoying the small pleasures of being a woman–like putting on makeup and wearing dresses.

    • In fact, the reality is such, that women do not get the same salary across any professions and across any functionalities 🙂 They might be getting the same titles at work, but they never get the same salary, even is Scandinavia, as far as I know, please correct me if I am wrong.

      Personally, I like it when a guy pays for me because I feel cared for, I feel safe with that man, it makes me feel that I can depend on him. Of course, this has to do with historically women being financially dependent on men. And, believe me, this kind of subconscious thinking will be very hard to eliminate. I bet Scandinavian women secretly love it when men pay for them despite the high equality between sexes 🙂

      And as an additional note. When I think about that, if it was me who initiated a date, I would feel obliged to pay. I have paid for my boyfriend’s tickets when I took him to cinema as a surprise date. It would have been if he paid for both of us in this case. See, I initiated the date, so I paid for it. Likewise, a guy pays for you when it is him who initiates the date. And as long as men will conventionally be ‘forced’ to initiate dates, they will be pressurised to pay for it as well!

  3. My fiance did all of the DO’s on our first date except that I did drive up to see him, but I didn’t mind, I like driving. And clearly it went well for him and for us! It left a mark on my mind that didn’t leave when I left and had been on many dates when the guys did the opposite. Chivalry is nearly dead but I believe that with your blog it will make a massive comeback. I love reading your posts, they’re great!

  4. Yes to all of this. I can’t tell you the number of times I have gone on a date and the guy is wearing shorts, and old t-shirt, and flip flops. Seriously? When I say no to a second date they are confused.

    I find that men don’t open doors for women any more and I will stand by the car door and wait. It is always interesting to see how they respond.

    I am single. Not because I have to be, but because the above has not been found in a single man yet. It does get discouraging, but I know they are out there and if all women would stop settling, men would step up their game.

    Women are equally responsible for chivalry dying.

  5. Some of these suggestions are great, but some are just dripping with try-hard neediness. Send a black car to pick her up on a first date? Not on your life.

    • Jeff, I used a black car service on a first date and my girlfriend and I have been together for a year and a half. Worked out pretty well for me.

      Like I said in the article, it’s got to be someone who you are *really* into and would appreciate a gesture like that. Not just sending cars to pick up every girl you want to have a drink with.

  6. Love all the advice but don’t necesarily agree with the last one about the kiss. I never kiss on a first date! No matter how much I like/am attracted to the guy. Kissing is intimate, it’s your mout on another mouth,and I wouldn’t want to be that intimate with someone I barely know. If a guy goes for the kiss I will turn a cheek but it doesn’t mean anything about where the guy stands.

  7. There’s a simple workaround for the rules about who pays: Get creative instead of defaulting to typical first date stuff like dinner and drinks. There are all sorts of fun things you can on your first time seeing a person with little to no cost for either party!

    • I agree with that on the first date. As to paying at other times, it depends on the occasion, and the event. Most men still do make more money than women, like it or not. So, that should be factored in fairly. Chivalry, to me is consistent, intelligent, observance, and practice in situations with fairness. It is easy to impress on a first date. Many persons open doors for people. I like this too. But, it does not determine long term compatibility, or worth of the whole person. The first date is a good place to start.

  8. I believe in the concept of chivalry, but personal experience dictates that always following these rules may hurt you on a first date with a lot of women.

    Today, good gentlemen have to deal with a delicate balancing game, of weighing traditional chivalry ideals against feminist ideals, and the ideal balance varies from one woman to another. That makes things a lot more complicated.

    First, it is important to remember (and ladies pay extra attention) that the meaning behind chivalry is more important than some superficial rules. Plenty of wolves-in-gentlemen-clothing know the rules too, and can easily follow them if they think it is to their advantage.

    Here’s what I think:

    1. Always have good manners and etiquette.The stuff about not touching your phones, and not getting drunk, is non-controversial and should apply to both ladies and gentlemen. Similarly, avoid colorful language and crude jokes. Tip generously. In general, be classy.

    2. Dress to impress, but be careful not to over dress. This is where the rules start to get complicated. Unless you specifically let your date know that you are taking them somewhere that has a certain dress code, you need to assume they may dress casually. If the gentleman dresses in a fancy suit, and the lady decides to wear a t-shirt and jeans, she’s going to feel awkward and he’s going to feel bad for making her feel awkward. The goal of chivalry is not to make your date feel bad. On the other hand, it should not hurt for the guy to dress 10-20% better than the lady he is dating, and that can make a good impression since she’ll realize he put some effort into it. That’s a good target to aim for. Just don’t go overboard if it’s supposed to be a casual date. As a rule of thumb, don’t go below smart casual.

    3. Paying has become the most tricky thing gentlemen face today, and hopefully most ladies realize this. The article ignores that a lot of women today do feel uncomfortable in varying degrees when a man insists on paying. Again, the goal of chivalry is not to make her feel awkward…

    So this is what I do. First, I always am prepared to pay. Second, I try not to make a big deal out of it since a date should not be about money.

    Ladies, for your part, you should not follow the advice in this article! Do not offer to split the check on the first date, unless that’s what you really want. Instead, all you have to do when he pays is smile and say, “Thank you.” Very simple. No true gentleman would ever have a problem with that. Then, when the 2nd Date rolls around, and he again tries to pay, that is when you offer to split it to be polite. At that point, he already knows you appreciate his generosity.

    But if on a first date, with no context, you offer to split, then he has to go through the agonizing process of sizing you up to see if you really want that or not. This can be completely avoided.

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