First Date VS Second Date

first date vs second date sized

First Date!


Key Factors

  • Find out if there is chemistry, or IOA’s – Indicators Of Attraction
  • You need to have the ability to cut it short if things go bad.
  • Make sure the date won’t cost a fortune.
  • Make sure your date is planned so there are little outside distractions (friends, work, family).
  • Don’t do anything risky or outside the box that could potentially hurt your chances.


  • Have a plan and don’t get caught flat footed. Ask her what she likes to do before the date, not during.
  • Go on an activity date. This takes the onus off you to be constantly entertaining.
  • Be funny! Women love a guy that can make her laugh.
  • Have fun and keep it light. No heavy talk or politics, keep conversation light and fun!
  • Get your adrenaline pumping – or include booze. Let’s face it; dates are stressful especially first dates.



  • Don’t include friends, yours or hers.
  • No double dates. First dates are hard enough; you don’t need to add extra pressure to it.
  • No sporting events. Sporting events are long and you need to make sure you can be next to that person for an extended period of time without feeling creeped out or bored.
  • Don’t go where you’re known by people. You don’t need people you know talking about your business especially when you don’t even know if you’ll see your date again.
  • Don’t continue on with a bad date out of obligation. End the date with class and style.



  1. Go on a bike date!
  • Example:
    • Meet your date at The ReCyclery Bike Café on 14th and Ogden, grab a cup of coffee and a homemade snack and chat for a while. Then fill up your water bottles and get ready to hit the road. Take it easy, you’re not training for the Tour De’ France, find a nice route to cruise that is quiet, scenic and conducive to getting to know each other and being able to talk. Bonus: Plan out a route that has some cool pubs you can stop in for a glass of water or a cold beer!
  1. Happy Hour on a patio!
  • Example:
    • I am a huge proponent of Happy Hour dates. The name says it all, happy and hour. Who doesn’t want to do something with the word happy in the name? And an hour? Perfect! Happy Hour is a perfect way to meet someone without having the expectations of spending an entire evening together. Don’t worry, if you hit it off you can continue the date, but if you don’t you have an easy out. I recommend places that aren’t cramped and dark; I like patios and wide-open places that don’t make you feel claustrophobic. People watching is a must, it gives you and your date something to talk about. Try Machete, Second Home, Marg’s Taco Bistro or Kona Grill in Cherry Creek. Govnr’s Park in Capital Hill is always fun and if you’re uptown give Steuben’s and the Tavern a shot. If the Highlands is your thing, try happy hour at Vita or Lola.
  1. Park Date!
  • Example:
    • Park dates are a great way of getting to know each other without breaking the bank and depending how much creativity you put into it you can really come across as a thoughtful person who put some effort into a first date. First, pick up a couple of delicious homemade sandwiches from your favorite deli and don’t forget to be ready to have fun stuff that won’t break the bank like a kite, Frisbee or anything else you can use for a fun park activity. A six pack or beer usually comes in handy, just in case. When you’re at the park I recommend trying the peddle boats. Peddle boats are a great way to get close to your date and have her undivided attention and have fun while you’re doing it! If all goes well, after your park date you guys can mosey on over to Wash Park Grill or Japon for apps and a beverage before you call it a day.


What you hope to accomplish on a first date?

  • Do you want to see her again?
  • What category does she fit in?
    • Friends
    • Attraction Only
    • Girlfriend Material


Second Date!

Key Factors

  • Looking for qualities and traits that are conducive to your lifestyle.
  • Seeing if your flirting is received well and escalates to romance.
  • Learn as much as you can about their situation, i.e., emotional availability, financial standing and any baggage that may impair growth.
  • Check for mental stability.
  • How much do you have in common?



  • Open up your wallet a little more. You can loosen up a bit more on a second date, chance are if she is out with you again and you didn’t spend much money on the first date she is out with you on a second date for the right reasons.
  • Plan more intimate dates that will make way for romance. First dates are to filter out the duds and second dates are to try and build a connection.
  • Ask more personal questions. This is the time to get the dirt without prying. Find out more about her in a casual way.
  • Learn about her family and past relationships. Knowing this stuff is big! I always say to people, take a look at their ex because that is your future.
  • Be honest and open. Nothing worse than starting out any kind of relationship based on false reality and lies. Be real!



  • Don’t try to impress her by talking yourself up or by throwing your money around. People that have it going on never talk about it and if they do, it’s very humble and brief.
  • Don’t talk sex. Be sweet and seductive but don’t be a pervert.
  • Put her in uncomfortable situations. The first few dates are uncomfortable enough, you don’t need to make it any more awkward by asking her to do or go anywhere that she could perceive as unsafe.
  • Don’t get drunk! Drink less than her or match her drink for drink.
  • Don’t try too hard. When you try too hard women can sniff it out in a second. That try too hard are usually in over their head and it’s a matter of time before it blows up on you.




  1. Rent Scooters! Step it up from the bike date and hop on some scooters and explore some beautiful neighborhoods in Denver. Scooters are great because you can still hear each other when you’re talking and you can be playful when you’re scooting around. If you’re looking for a scooter rental try Eaglerider Rentals downtown. Make a day of it and go grab lunch, I love to eat lunch at Watercourse on 17th avenue. Watercourse has a nice light menu so you’re not weighed down when you’re out playing.
  2. Along the same lines as a scooter date is something like go carts or bumper cars. Talk about fun and keeping the mood light, well this is it! I would recommend doing this on a first date but you know the drill, keep expenses low on a first date so when you do come across someone you like enough to go out with again you have a few bucks saved in your wallet. Try Speed Raceway in Englewood for the go carts and of course you can’t go wrong with Elitch Gardens for the bumper cars and more!
  3. Casual night out. Nothing fancy here, just well thought out fun. A casual night out can still cost you over $100 so you still need to maximize your value and time. Look for places that have multiple amenities in one place. Food, drinks and entertainment… Sporting event is great like a Rockies game or Broncos Game. Sporting events are great past the first date because you should know by now if you want to be seen or sit next to that person for the next 3 or 4 hours without losing your mind. Find a place like Ace on 17th avenue where they have ping pong or some other kind of activity like pool or bowling to fall back on if the conversation slows.


What you hope to accomplish on a Second date?

  • This is where you evaluate your ROI. If the chemistry isn’t there or you’re just not feeling it there is no need for a third date. This is where lots of people make the mistake for giving the benefit of the doubt. The benefit of the doubt leads to wasted time, money, effort and in some scenarios, backing your way into a bad relationship.
  • What category does she fit in?
    • Booty call.
    • Girlfriend material.


The first few dates are never easy especially if you don’t have a plan and go into them knowing what you’re looking for. Make sure you’re true to yourself and classy when you have to make tough decisions and remember, there is someone for everyone. If the situation isn’t right, don’t force it.


Greg Hollenback is joined in studio with Denver media personality Erin VandeVen for this installment of The Modern Dater! Greg and Erin talk about the coolest activity dates and places to go in Denver. Also the “Sheik” provides his philosophy on where to go on the first date, how to behave and how to proceed with second dates and beyond.


  1. ScooTours David says:


    Regarding scooter rental, the folks at Eagle Rider are great, but they can’t help you unless you have a motorcycle endorsement. For most of your listeners, they’ll need to call us at ScooTours Denver instead.

    As you can see at http://www.ScooToursDenver, all you need is a regular driver’s license that shows you are over 18, be able to ride a bike, and not be intoxicated. We will train you both to ride, and provide all of the gasoline, insurance, eye protection, helmet, lock, and suggestions where to go.

    We are very patient teaching the operation and safety information to new riders and we’ll have you take some laps in the parking lot until you are ready for a lap around the block to get comfortable. Only after you are fully trained and agree with us that you will be safe do we begin your rental time.

    Thanks for mentioning us on your program. It truly is a great date activity. Call for reservations. 720-523-3240 and learn more at

  2. Marvin in Aurora says:

    Thanks for the good article, this shows an unexpected amount of thought and intellect.

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