If you haven’t figured it out already, I am genuinely fascinated by human behavior. I did study Psychology in college along with Sociology, so I love to investigate and think about humans and how they act in a variety of settings. This post satisfies that itch in me.
Dating By Wegs
Rule 16: Take the Lead, but Be Flexible with Your Date
So, I hear this a lot from women. “I like a guy who actually plans a date.” I, personally, love hearing this because I take pride in figuring out a date for the person I’m going to see. However, the whole premise of the man planning the date for a woman harkens back to another time when a man took a woman out. In this day and age, most woman are working professionals just like men. So, in terms of financial resources, both men and women have the ability to pay for dates. Yet still, the traditional model of having a man plan a date for a woman and deliver on paying for the activities to me is the norm. There is something to all this with regards to gender roles and expectations. Let’s get real for a moment.
When I was single the last time in my 30s, admittedly, I was seriously broke. I mean I had just gotten divorced from a woman who made slightly more than I did. We were a dual earning household, and starting over that time meant a major adjustment in lifestyle. Plus, I was going to business school to get a better job. My buddies were all making a lot more money, and they didn’t have to worry about child support payments. So, in that era, I dated regularly, but I often looked to split the check as much as possible. I remember vividly having discussions with women at that time about splitting the check, and often times, I didn’t get 2nd dates as a result. So, I had to get more creative and smart about putting dates together. I still tried to plan dates, but I had to stick within my budget. That’s the real, real, Ladies!
As a more seasoned professional with slightly more discretionary income, I can plan more traditional dates and cover the cost. Now, paying for the date and planning are not a one for one relationship, but I feel like if you plan the date then you should pay for it. Here is where the Rule comes in. I think most women do respond to a guy who not only takes the lead to plan a date, but who is creative with it. Rule #1 Creativity Wins is 100% proven. Yet, there is no reason to not get feedback from your date or even let your date lead sometimes.
One of the things I love about dating is exploring the great city I live in – Chicago. This city never disappoints, in terms of things to do, even in the brutal winter (it’s like 0 degrees today!!). The truth is being single for 9 months now, I have only scratched the surface of all the cool spots to grab a drink or throw an axe or even listen to music. My research is based on internet searches and occasional conversations with people who know about something I’ve never heard of. So, there is no reason for us guys to not take the lead from a woman who knows where they want to go or more importantly knows better spots to check out.
The other thing to consider is that dating, like a favorite activity of mine – partner dancing, involves both people. Sure, one person should lead, but you have to respond to one another and the best dance partners feed off of each other to produce something better than what they do individually. To me, that is the goal of dating and ultimately relationships.
Here is the story: I’ve had a couple dates with a lovely woman lately. She is a superstar in her career and even has her own business on the side. We had gone out twice, and the weekend before last, I had to be completely straight with her about my financial situation.
We were communicating via text, and in doing so, I was intentionally being evasive because after the holidays, some epic dating runs and a party I threw, I was short on funds. Instead of just telling her that for fear of being judged by a woman for not being financially stable, I initially texted how “busy” I was. After a bit, I decided to pick up the phone and just tell her what was up. Not surprisingly for who she is, she was completely understanding about it and even suggest she pay for the next date.
Now the following week, we set up another date. I like to stick to my dating principles, and since we were going to go out to dinner and I picked the spot, I was determined to pick up the check. We hit a great spot in West Loop that my good buddy and podcast co-host suggested called RM Champagne Salon – http://www.rmchampagnesalon.com/. The ambiance is really cool, kinda like an eclectic living room in someone’s house – cozy, but slick. The food was great, and despite the din of the crowd in this smaller space, my date and I had a really nice conversation.
My plan for the night was to hit a place I really wanted to go to called the Blind Barber – https://blindbarber.com/pages/chicago, which is a literal Barber Shop that has a speakeasy component – a cocktail bar after 11 PM. My co-host buddy suggested it, too, so I was really excited to go. However our dinner wrapped up just before 10 PM, so my date suggested we hit a place in the River North area called, The Bassment.
Here is the moment of truth for me. Would I be ok with my date to take the lead and pick the next place? Admittedly, I was disappointed not to go to the Blind Barber, but we did have an hour to kill, so I said, “Yeah, let’s check it out.” We hopped in a Lyft (which she picked up) and got to The Bassment – https://www.thebassmentchicago.com/. The Bassment does have a small $10 cover charge, which I picked up. Then, we went down the stairs into this really cool lounge with a live band singing away.
We found a comfortable seat on one of the leather couches in the space. The band had a great female lead singer who was belting out anything from Aretha Franklin to Whitney Houston with a full band behind her. My date graciously paid for our drinks, and we got comfortable enjoying the music. As the night progressed, the music transformed into more old school R&B and hip hop, which I enjoy. This detour from the plans I had was a total winner, and I really enjoyed the Bassment.
What’s the lesson? I don’t need to lead, plan, and pay for every aspect of a date, especially on Date 3. I never would have known about The Bassment without my date, and given that eventually, I’m looking for someone who can be a partner, helping share the cost of a fun night was greatly appreciated.
So, guys, plan a date, but be flexible enough to flow with the evening, even if you do not control it. Be strong about taking care of your date, but it’s ok if you let the other person pay. Ladies, be like my date in understanding a guy’s situation, and let him lead if he takes initiative, but give feedback and detours are always appreciated.
Alright, good luck staying warm and discovering that cool new spot together.
Wegs