Last week I shared some ideas regarding how to generate conversations where you could learn about your partner through planned spontaneity. This week, I’d like to jump ahead to a point in the relationship after you’ve had a few dates or have been a couple for a short period of time. The goal is still to learn more about your partner. However, this ti it’s going to require a lot of planning. It could take several hours and is assuming that you’ve done your job during previous dates and have actually listened to things that she’s shared with you to this point. There is virtually no end to the number of variations for this adventure.


I’m going to use a park again for this example. In case you haven’t picked up on it yet, I’m sort of fond of the outdoors and parks in particular because the setting is so effective at creating a relaxing and fun-loving atmosphere.


Come up with a list of questions to ask your partner. It can be as few or as many as you like. In preparation for this date, take a stroll around the park to see what amenities are offered so that you can generate your list of questions. Each attraction should correlate to the question which will (hopefully) bring to light memories from her youth or plans for the future. It’s a scavenger hunt of knowledge. The best part is that you can answer the same questions so that you can learn about one other.


How you ask the questions is completely up to you, but here are a couple of suggestions.


  • Carry a map of the park with the questions written on the back.
  • Place an envelope with each question placed somewhere at the destination.
  • Stuff a question inside a balloon and have her pop it to read the question.


The types of questions you ask require careful selection and use of your memory. (You don’t want to ask the same question twice.) Pick your brain about previous conversations and dates that revolved around getting to know her. This is an added benefit to the pomp and flare for these occasions. The more memorable the occasion, the easier it is to remember. For example, let’s say your date was a soccer player in high school. Upon arriving at the soccer field, you could ask her about her favorite game, their biggest rival, any injuries she sustained during a soccer game, how she got into playing soccer – you get the idea.


Again, there is virtually no end to the number of variations this date can have, the types of questions being asked or the number of times you can repeat this event. The time and care you take to prepare for a date like this will, no doubt, bring a smile to your date’s face and help strengthen or build a strong foundation from which you can learn about one another. If you would like help setting up a date using this theme, please feel free to contact me and I will be more than glad to discuss variations based on your particular needs.


See you next week!


Spontaneity and thoroughness

This week is the start of something very exciting for me personally, and for this blog. In addition to sharing the creative ideas for dates and lessons on chivalry and planning, I’m going to be testing new theories and themes with real people. I’ve started an interview process with singles and couples alike, and each week I will share the results of dates that I have orchestrated. I’m going to focus on being thorough, planning and paying attention in an effort to make your date feel special; however, please keep in mind that none of the information I provide should be used as a mind game. I have no interest in helping anyone become a pickup artist. What I’m sharing is a way of life. It’s a way to help find (and keep) the love of your life. Take what I’m offering and apply it to everyone in your life, but make your woman the focal point.

There’s a lot to be said for spontaneity, but that doesn’t mean that we can’t have a plan from which unexpected activities are generated. Let’s say that you plan a low-key, romantic evening with your date a picnic at a local park, where children are playing soccer. A picnic in a park isn’t a new idea. On the contrary, it’s a popular venue for romantic dates because it’s effective and sweet; however, watching children play soccer can be extremely therapeutic on several levels. This may not be something that has crossed your mind before, but if you’re as fond of children as I am, watching children play can enhance your mood. It won’t add any pressure to the evening, and if you’re like me, it creates
excitement about the idea that maybe someday you’ll be in that same park watching your own children play.

This may seem a bit forward for the beginning stages of a relationship, but I’m not suggesting that you voice these types of thoughts. It does, however, present an opportunity to discuss having children without it being awkward or forced. You’re on a date to enjoy each other’s company, and to learn about one another. Whether or not your date shares the same desires about having children as you do, is a crucial part of any relationship.

When planning a date, it is important to be thorough, so take the time to research the park beforehand. Look it up on the Internet or take a stroll through several parks. Ask the park’s maintenance personnel about the plant life within the park, its history or special events that take place there. You can use this knowledge to initiate conversation, and it will allow you to learn things about her. For example, if this is a new relationship, you probably don’t know what her favorite flower or plant is. You can also ask if there is an ice cream truck that frequents the park. It won’t take much to find out the truck’s schedule, which can lead to additional opportunities for spontaneity.

Another way to create spontaneity in a park is to pack a soccer ball or Frisbee. Challenge your date to a game and make her laugh, but DO NOT let her win. It’s been my experience that a woman has more appreciation for a man who doesn’t belittle her by letting her win; however, there is no reason to beat the dog snot out of her either. While you’re goofing around, take the time to ask her about her interest in sports. What sports does she enjoy watching? Did she play any sports when she was a child? This conversation will transfer easily into one about her childhood, her goals, special events, etc. Do you see a pattern?

You are planning an evening that can create easy conversation; an evening that will allow you to be spontaneous, but will also make her the focus of your attention. (Women really like that.) Just remember, you have two ears and one mouth. You should use both proportionately.

Until next time….