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Wingwoman’s Guide for Men-First Three Dates

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Let’s be real, guys. It can be tiring to keep track of all the dating “dos” and “don’ts”. As your wingwoman, it’s my job to make sure you appear at the top of your game! Here is a handy compilation of the most important tidbits you need for a perfect date. Whether it’s your very first date and you want to impress the hell out of your girl, or you’re gliding through the second date and onto the third, you’ll find some useful information below.

 

This Reminds Me of My First Time

The pressure is on! Even if you and your date have previously hung out, worked together, or met through mutual friends, it doesn’t mean that the first date is any easier. It can be weird to think about sitting across the table from someone you like, and all their attention being on you. So loosen up! If you want some ideas for cosy date spots, you are more than welcome to hit me up for my services. I’m the ultimate wingwoman! I’ve got you covered. As such, here are some tips to keep in mind.

  • Be on time. In fact, be early. Scout out a laid-back environment, and arrive a few minutes early. For the first date, I wouldn’t suggest a fancy dinner just yet. Keep it casual. Take her out for some drinks around eight while things are still slow, and your wallet will thank you.

  • Dress the part. Confessedly, we are vain creatures. Don’t you enjoy getting checked out? Spend some time and effort on your appearance. Don’t wear a wrinkled shirt, but don’t go the extreme either and wear a suit. That’s a little overboard. You should wear a comfy button-down shirt, roll the sleeves up three quarters, and pair it with either a nice pair of shorts or trousers (but maybe not jeans if possible). If you need a second opinion, I’m your girl. My services as a wingwoman extend to making sure you look as good as you feel.

  • So tell me about yourself. Make sure you ask questions about your date, make her feel special. Pay attention to her, because she is special. Take turns asking questions, but don’t be robotic about it. Let the time flow. If she says something particularly interesting, don’t be afraid to ask follow-up questions to get more information. If you need some ideas on questions and icebreakers, turn to your wingwoman. I’m more than happy to help!

  • No phones allowed. Nothing is worse than having a wonderful conversation with a girl who’s obviously slaying, when suddenly your phone goes off. You see her eyes dart to your phone, where you have a notification from Tinder! This would never happen if you take care to have your phone turned face down. I’m not saying you should hide things from your date. But your attention should be on each other, not handheld glowing screens.

 

Give Me A Second

Now that you’ve won your date over, it’s time to start personalizing things a bit. You can start adding a bit more adventure to your dates. If you happen to be worried about how your date could go, it’s normal. Even if you aren’t overly confident with yourself, fake it til you make it. Smile, be attentive, and try to relax.

  • Pick you up at 4? With the second date, you have a lot more freedom. You have a better understanding of your girl, and the chemistry you have together. Instead of meeting at the place like you may have done for the first date, offer to pick her up at her place for a daytime date. Take her to a new place, perhaps even an activity you can do together. Take a walk in the park, visit an art gallery, play frisbee together, or go ice skating. The city is full of possibilities. Be creative, mobile, and have fun!

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  • Remember when? Demonstrate your amazing memory by bringing something up about last time. Perhaps she had noticed someone who looked just like Steve Buscemi. Maybe you want to remind her that you really want to meet her dog. Ask her how that work thing went. She will appreciate your attentiveness!

  • Change it up. Instead of just going to one place and chillin, keep the energy high. Have an activity or two, and then hit up a local deli to get some killer sandwiches. Even while you get the food, you can still walk around and share info between mouthfuls. It doesn’t sound super sexy, but hey. We’ve gotta eat sometime.

 

Third Time’s the Charm

By this date, you should be comfortable with her. You’ve had your casual drinks, and your laidback daytime excursions. At this stage, hopefully she’ll tell you if you have spinach stuck in your teeth at dinner.

  • Table for two. Take her out for a romantic dinner somewhere nice (but not too expensive). For ideas, ask your friendly neighborhood wingwoman (me!) if you can’t decide on a place. This might require some pre-planning (calling, making reservations), so keep that in mind.

  • We should do that sometime. Casually bring up the future. Not the sort of future where you want to be the father of her children or anything intense. Mention that your friends recommended this one restaurant/show/coffee shop, and say that you should go there sometime (together, obviously). This will make her aware that you want to keep her around.

  • You’re so unique. Women love to be told how rare they are. Don’t overdo it. Just briefly mention how amazing she is, and that you wish other women were as chill/cool/funny/refreshing as she is. She’ll be over the moon. Don’t overdo it though. Work it into conversation, when she says something particularly interesting.

So that’s the overall guide for the first few dates. If you need more in-depth ideas, I’m just an email away! My wingwoman services are at your disposal.      Good luck!

 

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