Happy New Year to Everyone!! It’s 2019 which means you have a fresh start in your life – new diet, new workouts, new clothes, but how about a new dating approach? Let’s start off 2019 on the right foot on the dating scene.

Dating By Wegs

Rule #13: Quality Is Always Better than Quantity

As you may have read in the Seasons of Dating Post (http://wegspool.com/2018/11/09/dating-by-wegs-the-seasons-of-dating/), traditionally the holidays bring on the big freeze when it comes to dating. However, my past experience in the dating world did not ring completely true this Holiday Season. The Great Hibernation has not set in yet, as the activity on the dating apps has actually increased of late. So, hopefully, you were able to enjoy some good dates over the holiday weeks. I speculate that when I was single about 8-10 years ago, the prevalence of dating apps was not around – smart phones were not as wide spread, either. So instant access may account for the surge in activity. I mean sitting around the fire with your family likely stoked embers of wanting romance for some – why not get on the apps to see if you can find someone special, right? I sure did, as I had like 10 days off of work. I, along with some other single guys I know, had a nice run over that holiday week.

However, there is a downside to all the activity. I mean as a guy, you always need to have multiple options out there when single. For the most part, men need to pursue the ladies out there (note: in a hetero world). Women can pick and choose. The mentality for guys is to have several options initially since you never know when one or multiple ladies will disengage and move on. Women usually have more than one suitor, in the traditional way, so they have more control as to who they want to spend their time with. I think the dating apps actually flip this concept a bit or at least level the playing field. Women and Men have the ability to swipe at any time to find someone new giving men an almost equal opportunity to have multiple suitresses (a word I just made up for female suitors) like women. It makes for a fairly disposable interaction, in fact. So, making a meaningful connection can be quite difficult. More on this in a second.

For a fairly recent single guy, always in my head I fight between the natural fear of scarcity (What Woman Would Actually Date Me?) and the previously discussed abundance principle (Relax, there are plenty of fish in the sea!). So, when I get a surge of matches on the apps, you can be sure I’m going to take full advantage of it. The only problem with that is you run into a “stacking” situation. Stacking is a concept that we all probably have done where we go on multiple dates in a weekend or even on the same day. From a time standpoint, stacking makes sense – we only have so much time on this Earth so make the most of it. Plus, over the holidays, a lot of us had time off to get together with someone new. I’ve done it plenty, now and in my past single stints. Yet, there are a lot of downsides to this.

There are 3 main downsides to stacking dates or even dating a ton of people in a short span. 1) It is hard to stay present in the interaction with someone when you have somewhere else to go or person to meet. Yes, that other person could be Mr./Mrs. Right, but what if this date you are on is incredible – why should you let the time end? Life is too short and aren’t we dating to enjoy our experience? Don’t short change the date your on for some possible future. Let the interaction flow naturally, and if it ends, then by all means, text or message that other person or meet your friends at the bar afterwards. 2) It takes a lot of energy to date. So, if you are stacking dates then ask yourself: “Will you have the same energy on Date 1 as you would have on Date 3?” Not likely. So, be wise in your time and energy and be open to giving all your dates your full energy. 3) Stacking opens you up to mistakes, slip ups and/or disappointments. Look we are human and will switch a name here or there (or country of origin in my case recently – Doh!). We may run late to a second date and have to be texting during the first date, which is never a good look. Plus, inevitably, it will be hard to keep the details about someone you just met straight in your head. So, learn from my mistakes and don’t try to fly too close to the sun when it comes to stacking those dates back to back or day after day (after day…).

In lieu of stacking, maybe try to designate a day or two per week for dates. That way you can plan ahead (always appreciated by your potential date) and be in the routine of being fully prepared for a date on that day. I think we all would benefit from getting quality interactions with one person a week versus 3 or 4 rushed experiences. But Wegs, what if that date sucks? Good question, but you can always make the most out of the date you are on and sharpen those dating skills – conversation starting, listening, and maybe actually learn something new.

A Total Exaggeration, but Here’s the Gist

Here is my story. As I’ve stated, I’m a habitual stacker. In fact, I think in my past single life I may have stacked 3 dates on the same day once…whew! Over the past weekend, I took full advantage of my days off and went on dates on 3 consecutive days with 3 different new ladies.

Day 1: Originally, I had planned to go on a walk through Millennium Park on a nice winter day and get lunch. However, the weather was crappy, so I opted for the Winter Wonderland Festival (https://navypier.org/winter-wonderfest/) at Navy Pier. My date was game for the change, and we met. She is a delightful person. We got along well from the start, and I give her big props for messaging me in Spanish the entire time prior to the date (she is a non-native Spanish speaker). We had fun ice skating, doing some carnival rides, and got a bite to eat. I had a great time, and I think in retrospect this was probably my most Wegs-like date – fun activity, good company, and good conversation. I’m not sure if we will go out again, but I enjoyed myself and getting to know her.

Day 2: The next night I had planned for a new person and I to meet at the Zoo Lights at Lincoln Park Zoo (https://www.lpzoo.org/zoolights-presented-comed-and-invesco-qqq). As the unexpected snow came down, she asked for me to pick her up instead of meeting there. We met and headed down there. I was surprised how crowded it was given the weather, and I was covered in snow rather quickly. My date was a great sport despite the weather, which was a big plus. We enjoyed talking and seeing all the light displays, in fact, we even were front row witnesses to a marriage proposal under the main arch of lights. My date took their picture, in fact, to commemorate the moment. After the Zoo Lights, I had a reservation at a nearby restaurant. The meal was lovely and she really opened up about her life. I can honestly say that the date was enjoyable, even if some of the information she shared was extremely personal. Maybe it was the snow and cold (or the 2 hours of sand volleyball I played before noon that day), but I was really tired after that date. I went home and just crashed.

Day 3: The next morning I got up and headed to the Logan Square area to a sweet brunch spot called Jam (https://www.jamrestaurant.com/) which my 3rd date suggested. My date beat me to the spot and had a table already. Of the three women, admittedly, I was most attracted to her. So, I was definitely engaged in our conversation. She is a very driven, accomplished woman, all extremely attractive qualities. I have to admit though, my energy was not at its normal level. In fact, about midway through the date, I told her I wanted to take her to do something fun. That was my personal way of telling myself, that I kinda mailed it in on this date. Brunch is a great first date, of course, but I was not my normal self, and my readers know I like to be creative. So, at least I recognized the need to give her a more Wegs-like experience. Thankfully, she seemed to like me and we have communicated since the date. I will hopefully, see her again this coming weekend, but the lesson is clear – stacking these dates even on 3 consecutive days had taken their toll (on my energy level and wallet….).

The bottom line is we need to put our best foot forward, and the best way to insure this is by being 100% present in the experience of the date. Yes, if I didn’t go on the 3rd date, then I wouldn’t have met a beautiful, successful woman. However, I was actually lucky I didn’t completely blow my one shot to make that first impression with her. I’m sure I was fine and seemed energetic, etc. to her. Yet, I know I can give her more than I did.

So, get out there and date, take your shots, but it is always best to take one great shot than 3-5 decent shots any day.

Have a great week.

Wegs