Sunday Sermon: Rethinking The First Date

Welcome to the Sunday Sermon where the topic for today is, yep you guessed it, first dates, and how to avoid the common pitfalls of a bad first meeting. 

One of my most memorable terrible first dates was with the owner of a fitness brand. He picked me up in his fancy car and revved the engine at every light, went about 110 mph on the freeway and started and stopped with such vigor I thought I might throw up. We went to a loud, crowded bar/restaurant to get barbecue and he checked his phone what seemed like every 3-5 minutes. He then proceeded to bash American sports (my team was currently competing in the NCAA tourney) and body-shamed some of the women who were "housing the ribs." We then went to the movies where he proceeded to try and put his hands down my pants despite no green light whatsoever. 

Giphy Images.

We never saw each other again. 

Despite him being an arrogant asshole, there were actual elements of the date that prevented connection even if he wasn't actually an absolutely rotten douchebag. I hope to break some of these things down and give you some things to think about before you plan your next first date so hopefully, you'll make it more smooth and can get to that second date, and maybe from there to the promised land. 

You may be thinking "Trysta it's really not that deep, why do first dates matter?" I think the way a first date goes is about as important as dating gets. If this person has never met you before in real life (in the age of dating apps), this first impression will make or break whether you ever see each other again. Can't have a second date without the first, and if you're looking for a relationship and it progresses to that level, this first date will be a memorable one. 

Given how critical this first date is, I think the trick is to approach it with the mindset of making each other as comfortable as possible. You want to be able to assess the connection and compatibility, so the stiffer and more formal the setting, the less likely you'll see who that person really is. 

That brings me to one of the most important elements to think about. 


Let's use the BBQ spot as an example of what not to do. It was LOUD in there. It was crowded. Hard to get to the bathroom. Hard to get the server to pay attention to us. The air was smoky. The food was MESSY. Almost couldn't have been worse. Not only could we barely hear each other, but the vibe also put us both a tad on edge. I was annoyed 5 minutes in. Not good. 

In my opinion, an outdoor venue with light drinks and snacks is a great way to get to know one another. It's low pressure, allows you to hear one another, and typically the servers leave you alone enough where the conversation doesn't constantly get interrupted. 

If you live in an area where this is possible, I would choose a place (not a chain) that you have been to multiple times before and know is solid. If you're a guy reading this, choose a place with a wide enough menu that will fit a variety of potential dietary restrictions. The last thing you want is her to say "uhhh I can't eat anything here" and then you have to find somewhere else nearby while she's hungry and nervous and annoyed. As a recovering vegan, I've been hungry in a carnivore's paradise and vegetarian's desert and I was PISSED. If that's a way for you to weed out vegans and picky eaters, fair enough, just be aware of the potential blowback. 

Another trick is to choose a location that's close to your house or if you have plans later that day, somewhere near there. This will make you feel comfortable enough to show them around the neighborhood if they ask about the area and if it goes REALLY well, maybe it leads to some drinks back at your place. If it goes horribly, it's just a hop, skip, and a jump back to the crib. 

One more idea for a date if you REALLY like this person and want to give them a memorable experience. Go somewhere eclectic like an aquarium, a street fair/ art walk, zoo, etc. This type of location gives you something to talk about and have unorthodox conversations like "why do monkeys fling poo" vs the "what do you do" and "where are you from" type of boring first date questions. 

This leads me to another tip. 


The most important element of good conversation is being engaged. Being engaged means doing your research ahead of time (looking at his/her IG for conversation starters), being curious, LISTENING, adding to the conversation and bouncing it back with another question. That keeps the flow going versus dominating the convo, or on the flip side, not contributing at all and seeming disinterested or worse, not interesting. If you can, share a funny or vulnerable personal story about yourself. That level of vulnerability or openness can give the other person permission or comfort to do the same. 


Speaking of comfort, let's talk time of day.

I personally advocate for weekend day dates. It keeps the pressure low and creates a casual atmosphere that leads to a comfortable conversation. The day-date also gives you leeway for a short date (coffee, drinks) or a longer one if it goes well. If things immediately don't click, you always have cover to say "oh I need to finish up some weekend work" or "I have evening plans with some friends". Again, it's all about creating a cozy vibe that brings out that person who may be shy or slow to show his/her true personality. 

Finally, and I could go on about these but I won't, here's a list of some dos and don'ts for a fruitful first date. 


  • Be late. Nuff said
  • Use your phone. Turn it on do not disturb and hopefully out of sight if you can
  • Talk about your ex. No no no. 
  • Talk about the future. No one wants to hear about how many kids you want or that you're just looking to hook up on the first meeting. 
  • Ask too much about their work/job. This is a romantic endeavor not a networking function
  • Talk politics. I mean… things could get ugly
  • Pepper them with questions… one after the other. Again, this isn't an interview. 
  • Act like someone you're not. The truth will come out sooner than later anyway.
  • Overshare. We all know that person that gets drunk and tells you the dirty details of their trauma. Do not be that guy.
  • Brag. If they mention they've been to London, don't follow it up with bragging about how you've seen every European country and Asia is way more interesting
  • Be mean to the waitstaff. Nothing worse than this. 
  • Get too drunk: A huge mistake. One drink to settle your nerves is fine; getting Dana B'd on a first date is a definite no.


  • Listen: Easy one. You're trying to get to know someone, not listen to yourself drone on. 
  • Relax: I know, I know. Easier said than done, but the more calm and relaxed you are, the more calm and relaxed they will be. 
  • Make Eye Contact: No one wants to look over dinner and drinks and see you staring down at your flank steak instead of looking back.
  • Be honest: Don't lie. Best case scenario, it comes back to bite you in the ass. Worst case it blows up in your face immediately.
  • Smile: Act like you're having fun for God's sake! 
  • Try your best to make them comfortable: This date is about measuring your compatibility. If you don't make them feel comfortable and at ease, there ain't going to be a second date, and you'll go back to humping your left hand.

So there's a few tips on how to get better at first dates. Because the truth is, every great relationship starts with a first date. The sooner you start getting good at them, the quicker you'll get to having your last first date ever… unless you like the whole process of awkward new meetings… I mean that's a thing too I guess.