How to Not Suck at First Dates

leia date

Ahhhhh, the dreaded first date!

Your palms are sweaty, your arm pits are sweaty… okay pretty much all of you is sweaty. Wandering into the unknown, your head explodes, imagining every possibility: Is this date gonna suck? Is it gonna be awesome? Is this going to be the person I spend the rest of my life with? What if this or that happens?

For so many Rebels I’ve talked to, trying to get healthy is closely related to our hopes of finding someone special to spend our lives with. It certainly influenced why I started getting healthy and has continued to play a role in my decision to exercise!

Having been on my fair share of both amazing and cringe-worthy first dates (way more of the second one than the first), I feel like I have a pretty firm grasp on how to kick ass at first dates.

No falsifying yourself… no being somebody you’re not. Instead, we’re just going to present ourselves in the best light so we have the best chance to make a real connection with somebody.

Here’s how to stop sucking at first dates and go in with confidence.

Where Does One GO On A First Date?

wine date

You may not think it, but where you go on your first date can have a HUGE but subtle impact on how things go. It can also be the difference between a real connection and a train wreck of an evening.

Let’s start by determining how you met each other: Was it through the internet or a dating app? Is he/she the friend of a friend? Did you meet at a bar, party, or use 20 seconds of courage to ask out that cute someone in line at the coffee shop?

This will dictate the type of first date you want to have. The point of the first date should be to determine if you have a connection with somebody (not fall in love right there).

1) IF YOU HAVEN’T MET THIS PERSON IN REAL LIFE YET:  My recommendation is to start with coffee, a drink, or something light hearted like meeting at a park. NOT dinner and NOT a movie. There’s nothing worse than learning within 5 minutes of meeting somebody that you’re not a good fit, only to have to sit through a three hour dinner or sit in awkward silence next to them at the movies. This is why I like drinks or coffee. If it’s going well, there’s an attraction and conversation is coming easily, you can order another. If not, you can politely decline another round, say you need to get going, and bow out gracefully, saving you both from an uncomfortable evening. If you aren’t sure what type of date to plan, err on the side of this category.

2) IF YOU HAVE ALREADY MET THIS PERSON IN REAL LIFE: Consider the above options, but also consider something a bit more adventurous if you already know this person and have talked about something you both enjoy (swing dancing, a museum), etc. If you know there might be some connection or shared interest, you have some extra room to venture out from the low stakes, playing-it-safe method above. A museum, rock climbing gym, a stroll in the park, or something a bit quirky that you know you both enjoy.

3) EITHER WAY, DO NOT FLAKE OUT: Be a person of your word – if you commit to a date, go on it. Don’t say yes, and then text them later and change plans and bail on it. If you don’t want to go out with somebody, POLITELY DECLINE FIRST. I don’t know why we think that saying yes only to say no later is better – it’s not and makes you a crappy person. Texting makes this pathetic practice an easy out. Aziz says it best:

Okay, so now that you know WHERE to go on your date, it’s time to get prepared for that date. You need a solid battle plan.



Like any great war or battle, most of the work is done before a date starts. No, I don’t mean stalk the person you’re going to date and know everything about them. In fact, I recommend not internet-stalking your date! It’s far better to get to know somebody from talking with them rather than pulling a: “so I read your Facebook page and looked through your photos, tell me about your trip to Guatemala in 2010! Also you looked nice in the red dress in March 2013.” What I really mean is making yourself a worthwhile first-date (and beyond) candidate!

Take care of your appearance: This starts by taking care of yourself physically – if you’re here reading NF you’re already taking steps down this path. Yeah, your mom says “beauty is only skin deep,” and “don’t judge a book by its cover.” HOWEVER, in reality we judge people every second of every day, and we are going to make a first impression (good, bad, or weird), on EVERYONE we meet. Might as well put our best foot forward and show our best side so the kick-ass parts of us (what’s inside DOES count) actually gets a chance to shine. Now, a huge part of this is…

Dress the part: Dress appropriately. When in doubt, go a bit too formal rather than a bit underdressed. It could be a sport coat for guys or a dress/skirt for women. Better to look a bit TOO stylish than like slightly on the slob side of things. T-shirt and flip flops is great for the beach, not for a date. Obviously this depends on the date you’re on (drinks vs. rock climbing), but take care of yourself.

Want to learn how to not dress like an idiot? Read this (our article on not dressing like an ass). A word to the wise for all: dousing yourself in axe body spray/cologne/perfume is not cool.

“But Steve my style is this nerdy t-shirt and these holy jeans, and I want to be me.” I hear you, but remember that this person is likely going to judge you instantly before you say a word, and if you want to have a chance to share your awesome, quirky personality, it has a better chance if it’s packaged with a solid outward appearance. Think comfortable and designed for your body type!

Be interesting: This gets better with practice, but you become way more interesting if you do more things than “I work at Innotech, and I like TV.” I can’t tell you how many dates I’ve been on with a woman who said “Well I go to work, and I love to watch Netflix.” Hard pass. No matter who you are and what you like to do, there is something more interesting about you than the last thing you queued up to watch.

DO NOT LIE TO SOUND COOLER. You CAN, however, learn how to present yourself in the best light that makes your story more interesting. Which person would you rather hang out with?

“I work in IT. I like Netflix. I sleep in on weekends. I drink a lot.”

“Well, I work in the technology division of my company, but I spend my free time hiking with my dog, Rebel. I’m trying to learn to play the guitar because it looks like fun. I just started planning a trip to Croatia because I want to check out Plitvice Lakes.”

Remember: You’re not bragging, but sharing the real you in an interesting way. Not just where you are now, but where you are now and where you want to go. This means not just the “I work here” nonsense. That’s boring and doesn’t define you. That’s a box that we’re taught to put ourselves in. Be better than the box.

Okay, we’re ready for the date!

What the Hell Do I Talk About?

“Steve! Help! I suck at conversation and I don’t know what questions to ask and I hate awkward silences. AH!”

The point of a date is to get to know somebody and see if you have a connection, so you want to create some back-and-forth (like a playful volley in tennis) in which you’re both asking questions of each other and answering their questions with more of your own.

These are the two extremes you want to avoid:

  • Avoid feeling like you are conducting an interview. In these less-than-optimal dates, every question got a one-word answer or two. If somebody is asking you a question, feel free to explain your response with a “here’s an answer, and here’s why. What about you?” This helps avoid the following:
  • Don’t let THEM ask all the questions. When I end up doing all the asking on a date, I learn a LOT about the other person (mostly that they’re selfish or unaware), and they learn next to nothing about me. And I leave those dates with the impression, “Wow, she went on forever and ever and never once asked me a return question.”

For us introverts, it can be tough, but memorizing a few fun questions can be really helpful in getting the conversation started. These are my go-to questions after we’re in the conversation a few minutes – the sooner I can get past the small talk stuff and REALLY learn about somebody, the better:

  • If you could wake up anywhere in the world tomorrow, where would it be?
  • If you could only eat one meal for the rest of your life, what would it be?
  • If you could have any superpower, what would it be?
  • What’s the best concert you’ve ever been to?
  • What’s your favorite guilty pleasure song?
  • If you could be the best in the world at one activity, what would it be?
  • What’s the most exciting thing that happened to you in the past week?

Notice in each of the questions above, you can follow up their response with a “that’s really interesting, why?” and provide your own thoughts, and it becomes a conversation instead of an interrogation! Yay nerd conversations.

Meanwhile, it might be a good idea to be aware of some questions and topics NOT to venture in to right away:

How to Not be an Accidental Ass

frog love

Now, as you’re going on your date, I wanted to share with you some tips on how to be a great first date. You’re not just evaluating them, they’re evaluating you, too! Even if it’s not a love-match, you should still be respectful and remember that they’re a real person with real feelings… just like you.

Here are a list of things that will make you an accidental ass on your date:

1) Checking your phone every five seconds. This is an instant “you’re an ass” moment. Put your phone in Do Not Disturb mode, and don’t check it while you’re with your date. Put it in your pocket, leave it in the car, whatever. Life will be fine without your phone for 90 minutes, I promise.

2) Not being present in the conversation. That person across the table from you chose to spend their time with you instead of doing any number of other things, and for that they deserve your complete attention. Be sure to make eye contact and respond with questions or comments that show you’re actually listening to what they’re saying.

3) Assume the other person will pick up the check. I’m old fashioned and don’t mind picking up the check if I’ve asked a woman out, but it’s nice when they ask “want to split it?” before I get a chance to grab it. If you’re on a date don’t assume the other person should pay, especially if you asked him/her out, or it’s a first date from the internet/an app. When in doubt, ask to split it. If they insist on paying, let them and tell them you’ll get the next one.

4) Getting way too drunk. I don’t care how bad your social anxiety is, don’t show up to your date blasted. Don’t get blasted while ON the date, unless you happen to have picked “drinking contest” as your first date.


5) BE RESPECTFUL: Dating sucks sometimes. A lot of the time, actually. Sometimes you end up on a date and you know pretty quickly that it’s not a good match. Conversely, they might be having the same thought.

It’s nothing personal (though it’s really tough to NOT take this personally), but when it comes to first dates usually it’s pretty obvious within 5 minutes if it’s a complete miss (especially if there’s zero physical attraction). This goes both ways.

I’ve never walked out on a date, but I have heard horror stories from people who have showed up for a date only to have the other person walk out or say “sorry this isn’t gonna work” and bail.

This is crushing, and I would advise against doing it because it can really hurt somebody. However, if it happens to you, take solace in the fact this is somebody you were not going to connect with anyway (plus, they suck) and they just helped you save a few hours of your time. They’re an ass.

Again, this is why coffee or ONE drink is perfect for a first date. An hour is plenty of time to know if you want to spend more time or no-more-time with this person.

What Happens After Date ONE?


YOU DID IT! You went on a normal date. Great work. Now, what happens next?

IF YOU THINK THE DATE WENT WELL: After the date, a simple text the next morning like “Hey, I really had a great time hanging out with you! [Some comment about a joke/story told while on date: “Glad to find another Zelda lover!”], let’s do it again soon?”

Don’t sit by your phone and wait to see if he/she responds. Yes, they got your text.  Don’t send more texts, which is the modern equivalent of Mikey in Swingers:

Trust me, they read your text. Immediately. Have you ever just not read a text from somebody? OF COURSE NOT. Here’s what to do:

Did they not respond? They got your text. They may respond declining, or more often than not will just NOT respond. If they were interested, they would get back to you. Move on.

Did they respond with a fun INTERESTED message? Something like “I had a blast too! Thanks for blah blah blah.” ? Great, it’s time to ask them on a second specific date: “There’s a concert on Wednesday/Want to grab dinner on Tuesday?/Let’s go to the park and toss a frisbee around on Friday afternoon?” Your response does’t have to be instant, but don’t play the waiting game either.

Did they respond with a wishy-washy text? Now, what if they respond with something like: “That sounds like fun but I’m busy then!” Use the following technique (hat tip to Art of Manliness!): If they makes up an excuse and don’t suggest an alternative plan, ask yourself “If I was Chris Evans or Scarlett Johansson, how would they respond? They would make time or change plans or suggest an alternative.” If they are noncommittal, they are not interested and are avoiding confrontation. If they wanted to see you, they would make it work.

If you feel the date didn’t go well:

  • Do not go on more dates simply because you don’t have other options.
  • Don’t be an asshole: UNDER NO CIRCUMSTANCES should you make more plans with this person and continue to text them, break plans later, or say “I’m too busy,” so you can avoid the awkwardness of shutting them down right away. It’s not fair to them, and it could be keeping you from meeting somebody you actually connect with.

If they reach out to you and ask for another date, and you know it’s not going to go anywhere, please do the kind thing:

  • Let them know you had fun but it wasn’t a fit. This makes you a kickass person in my book. Just let the person know “Hey, thanks I had fun tonight too. You’re awesome, but I didn’t quite feel the spark – good luck out there!”

Even though you won’t always receive this kindness, please represent nerds everywhere. And when this doesn’t go your way, as someone who has been dumped by many who haven’t reciprocated, my best advice is to look at each opportunity as an experience to learn.

Maybe our stories aren’t that great! Maybe we were distracted and didn’t look invested. Maybe we talked too much about ourselves. Maybe we didn’t take care of our appearance. Or, most likely, maybe we just weren’t a good fit for each other.

I’d love to hear from you. Any tips for your fellow rebels who are looking for love in all the wrong (or right?) places? Any horrible first date stories you want to share?

What else can I help you with in your quest to turn life into a Co-Op Game?



photo source: thelittleone417: wine, Pedro Vezini: Leia, Kristina Alexanderson: Storm Trooper

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