Want To Plan A First Date But Not Really Sure What To Do?

I have a certain way I like to approach planning first dates. I actually refer to them as “pre-dates.” To me, real dates start after I’ve decided 100%, ok, this is someone I’d like to spend time with and to get to know.

Pre-dates are simple.

It’s coffee, drinks or sometimes dinner. Any mature adult can manage a simple one-hour date with a stranger. With this goal in mind, I can go into a date feeling no pressure. All I have to do is be myself, hope my date is himself, have conversation and hope there’s a vibe. I use this pre-date as an opportunity to see what the person I’ve been texting really looks like, how they talk, interact, and to gauge their personality.

To me, this mindset takes a huge load off.

These are the steps I take when planning pre-dates:

  • The goal of online dating is to get offline. I don’t mind a little bit of messaging chit chat, but let’s get the date planned already. With a day or two, tops, I want to get plans made. I’ll stop talking to a guy if takes too long to get a date scheduled.


  • I always plan these dates during the week, after work. I don’t usually have special events planned during the week. Most nights I’m at home doing my own thing. So, I like to plan my pre-dates on nights I would otherwise not be doing much.


  • I always suggest meeting at the same place. I like to take the lead in choosing the location. I do this for comfort and safety’s sake. I pick a place that’s near me and one that I’m familiar with. If I’m meeting a man who lives a good distance away from me I will find something halfway. If the man I’m meeting makes a suggestion, I will research and I will approve. If I don’t like his idea, I will suggest my place. If he gets fussy, I will cancel (this has never happened).
      • The place I choose is nice but casual. I want to wear outfits that are cute, but comfy. I wear something I know fits me and I look good in. If I feel comfortable then I will be comfortable.
      • What I like best about this place is that it’s a bar/restaurant. I always suggest we sit in the bar area because if we are enjoying our drinks and conversation then we can then turn drinks into dinner. If things are falling flat, we can skip food and wish each other well.
      • This strategy of mine also works well price-wise. I offer to chip in, but the guys always end up paying. Something I am deeply grateful and appreciative of. I’d rather avoid the added cost of dinner on behalf of the man if we’re not really jiving.


  • On the day of the date, I always tell a friend or two where I am and who I am with (by this time I know the full name of the guy I’m going out with). I also text them when I get home.

Once the date is happening, I let it flow naturally, but they usually last about an hour. I think that is a decent amount of time to get to know someone well enough to know whether I want to go out with them again.

After one or two pre-dates, and I know I really like someone, and they like me, I’m ready to schedule a more elaborate lengthy date. I’m open to planning dates on the weekends, going for a drive and picnic, a two-hour hike followed by a beer, a movie followed by dinner, grocery shopping and cooking together at home, and so forth.

The longer more “experience” type dates are when two people really start to connect and build. This is when things really start to get fun. Now you can start thinking, what kinds of experiences do you want to create with the person you’re dating?

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