Let’s prep for your online date!


Whether you’re trying out online dating for the first time, or an old pro who needs a little advice about prepping for first dates. First dates, no matter how many you’ve been on, are no picnic. Getting someone to hold a conversation with you, getting to know them, building a rapport and finally, getting to the date planning stage are already pretty exhausting, and then to actually put in the work to get a first date on the calendar? It ain’t always easy.

So, with that in mind, I wanted to write this guide for you. I’ll break it into 3 sections:

  • Pre-Planning
  • Planning
  • Execution



Many people are reluctant to give out their phone number for date planning, with good reason. Think of all the apps you use where your phone number may be saved, or used to look you up. Many people add their phone number to Facebook, Instagram, LinkedIn, and so on. With your phone number, someone could easily find you on all those sites, and many of these sites include personal or professional information about you that would make it easy for someone to find you in real life. By the way, please, I beg of you, stop including specifics about your job on dating apps. Remove your company name, and only use a generic job title. If I know your name is Jane Doe, who is a Bartender at Shots O’Houlihan’s, I know exactly where you work, and can show up at your job, even if we didn’t match. Be smart, and be safe out there, kids. Sure, most people are harmless, but a percentage of people are not. I’m not saying that you shouldn’t give out your phone number, or not use dating apps in general, I just want you to have an idea of what your risks might be. If you’re worried about what people can do with your phone number, which is a valid fear, there’s nothing wrong with figuring out all your date planning on whatever online dating platform you use and deciding to exchange numbers if you hit it off. On the other hand, some people will be wary of someone unwilling to give out a number to date plan, since it’s often a red flag that the person in question is a catfish, or not serious about meeting. If you’re hesitant to give out your phone number, but don’t want to risk appearing to be a fake user, I would *highly* recommend signing up for a Google voice number. It’s free, can be used to call or text through the Google voice app, and functions like any cell phone number would.

Alternatively, you can be like me and just give your real number out. It rarely backfires for me, but bear in mind that I’m a straight man who does a very good job of filtering before I go on a date. Results will vary. If you’ve ever gotten an unsolicited dick pic from someone you gave your phone number to on Tinder, give the idea some thought is all I’m saying.

If you do decide to date plan by using your phone number (or a phone number) texting works just fine for most people. If you’re one of those people who would prefer to plan a date over the phone, mention that. The more and more texting becomes the norm for people of all ages, the less likely you are to meet people who would prefer to date plan via the phone. Just something to keep in mind.


Once you’ve figured out whether or not you want to share your phone number, it’s time to start date planning. When it comes to date planning, or dating in general, many people do not have the same ideas or expectations. While you might adhere to more old-fashioned gender roles, many people do not share those values. Many of these same people would be okay adhering to them when it comes to dating and date planning,so be upfront about what you expect. If you’re a straight woman who believes that men should always plan first dates, SAY IT. Not everyone dates the way you do, nor have they had the same dating experiences. If you want someone to take the effort to plan a date and it isn’t happening, there isn’t anything wrong with saying “Can you plan this date?”. It’s entirely possible that he isn’t planning the date because he doesn’t want to put in the effort, but it’s also possible that he assumed that you wouldn’t want him to. Or maybe he assumed you wanted it to be collaborative. No way to know for sure, so just be vocal about what you want in the planning phase.

When planning a date, consider distance and convenience of travel, for you and your date. Let’s say, I’m going on a hypothetical date with someone who lives about 30 minutes into Queens from Union Square, and I live about 30 minutes into Brooklyn from Union Square. Planning a date closer to me would be inconsiderate of both distance and convenience for my date, and planning a date closer to where she lives would be an inconvenience for me. In this case, I’d plan a date at or around Union Square, since it’s equidistant for both of us, and convenient for both of us to travel to. In lieu of a suitable date venue that is equidistant for either of you, at the very least choose a first date venue that is relatively easy for you and your date to get to.

Many people, specifically men you’d classify as “nice guys” try to plan dates that are convenient for their date to travel to, but a huge inconvenience for them. Don’t do this, especially on a first date.

As for the date venue itself, I have two recommendations. Never go to a venue you would avoid normally, and never do an activity you know will make you uncomfortable. It’s incredibly hard to have a good first date if you’re uncomfortable, or if you hate the type of venue you’re in. I may be on the fence about coffee dates, but I know for a fact that I never want to go to a nightclub on a first date. A nightclub. Also know that I never want to have a first date that involves interactive theater. You probably already know what sort of venue you don’t want to go to on a first date, and you probably have an inkling of what first date activities wouldn’t work for you. Whatever they might be, never do them. If you, like me, never want to go on a first date at a club, and someone insists you do, otherwise they wont go out with you, they’re probably not a good fit for you anyway. Better to miss out on some first dates you know you wont enjoy than to go on ones you know you’ll hate. One caveat, if it’s something you’re not sure if you’ll enjoy, might as well give it a shot. I’ve been on a first date in a club, and I hated it, and now I know I’ll hate it.

I’m not saying you shouldn’t experiment, but if you know you know you don’t like something, stop doing it to please other people.


Three tips for you for right before, your date:

First, avoid trying to go above and beyond on your first date. Dress to impress, but don’t buy a new outfit or anything. Wear something you think you look good in that won’t make you uncomfortable. Show up showered and groomed, but don’t try to over do it, like trying a new grooming technique specifically to impress a date. I used to buy a new shirt for each first date I went on, and while it was a great way to get new shirts, it usually backfired because I either felt uncomfortable, or I put expectations into a date going well because I’d already invested money into it. Remember that the person you’re going on a date with saw your pictures, read your messages, and wants to meet that person. The current you is good enough for them, so don’t show up trying to be something or someone you’re not.

Second, never treat someone differently because of how attractive they are, or how well you think you’ve connected. Lots of people, especially “nice guys” do this thing where they assign a higher value to someone based on their looks, or how much they have in common before a date, so they try to go the extra mile to impress them. I’m a big believer in doing things to impress someone you’re dating, but not on a first date. A first date is where you figure out whether or not you ever want a second date, so it’s not the date to show up with flowers, you know?

Finally, this seems like it shouldn’t need to be said, but I’ll say it anyway. Keep track of who you are on a date with. It takes a really small amount of effort to keep track of the basics about someone you’re going on a date with, but you’d be surprised by how often people put hardly no effort into remembering the basics. Before a date, quickly check out their profile and your messages to remind yourself of the basics. It’s a small thing that will take maybe 5 minutes at the most, and will spare you no small amount of embarrassment. Not sure what I mean by “basics”? Here’s a really simple template:

  • Name
  • Age
  • Profession
  • Hobbies
  • Where they’re from?
  • Where do they live?
  • What conversations have you already had?

Here’s what it looks like in practice, using me as an example:

  • Demetrius
  • 31
  • Writer/Podcaster
  • Writing and Watching YouTube videos about Physics
  • NYC
  • A very long conversation about Werewolves, for some reason

At the very least, that quick bullet list will give you a good reference point for remembering who you’re on a date with, and at best,it will give you some new conversation threads to follow-up on. For example,  “So tell me, why’d you get in podcasting” or “What is the deal with your obsession with Lycanthropy?”.

Above all else, remember to have fun, be safe, and remember that even the best of us go on bad first dates, regardless of how well we prep for a date. Online dating is just like offline dating, in that all the preparation in the world will never guarantee that you’ll NEVER go on a bad first date. Sometimes it works, and sometimes it doesn’t, and the best thing to do is to keep a level head, date the way you want to, and try your best to have a good time with minimal expectations.

Good Luck Out There.


4 thoughts on “Let’s prep for your online date!

  1. I literally “awwed” out loud (AOL?) when reading you used to buy new shirts for all your first dates! The pre-indifference days! And this is a great post. I’m really bad at remembering the basics…I rarely re-visit a profile before going on a 1st date…you’ve got me thinking maybe I should change that…

    Liked by 1 person

    • Yes, a young Demetrius in his pre-indifference days was way more “aww” worthy that’s for sure, but way too much for most women on first dates. Learning to be chill helped.
      And yes, always a good idea to do a quick refresher. I’ve always found that it helps if the convo stalls


  2. All good advice but I’m so glad you said what you did about putting your name AND name of your company. I like for there to be as much anonymity as possible in the beginning (especially if I don’t know I want to meet you) and putting all that info is just asking for someone to look you up/locate you. I’ve had way too many scenarios where I stopped chatting with a dude on an app and weeks later I get a FB or LinkedIn (ugh) request from them. NO.


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