For those loyal readers of my blog, you know that if I do something like Dating, then I’m going to go all in on it. I mean if writing a blog is not enough, then why not take it to another level. More on this in a second.

Dating By Wegs

Rule #15: Meet the Old Fashioned Way

What is wrong with meeting people the old fashioned way, anyway? I mean before like 2010, no one was using Tinder or Bumble to meet people. Before 2000, no one was using Match.com. I suppose there have always been newspaper ads, and incidentally, I believe my dad met his current wife through such an ad in the early 90s. Still, truthfully, there is really no substitute for meeting the old fashioned way.

So, Wegs, how do you do that in this modern world? Well, that is a great question. In my 30s, when I was divorced the first time, I hit the bars with my softball buddies almost every weekend. My one buddy literally had to get an auxiliary back up to keep all the numbers he had in his old flip phone. We affectionately called it the Bat Phone, because when he opened it the blue light from the thing projected all the way to the ceiling. I always admired that guy as he was the consummate “opener” in a group of ladies. He was fearless in just going up to someone and starting a conversation. We, as good wingmen, immediately swooped in to talk to the point woman’s friends and the night began.

Now, not everyone can be my friend, but I think there is a lesson here. The key to meeting people the old fashioned way is to initiate conversation. I mean the classic spot is at a bar or street festival, when you just strike up a conversation with someone. That is why back in the 70s and 80s the smoother operators had those stupid lines they used to use like, “Are you injured?” The woman replies, “No, why?” Dude responds, “Because I thought you were an angel who fell down to Earth” or some ridiculousness like that. Still as a guy, you are taught to take your shots. Even with a 5 or 10 percent success rate, that means all you have to do is use that trash on 10-20 women to be successful. I’m not advocating for that cheese ball line stuff, but I think most women and I would guess most men for that matter, respond to confidence and direct confidence. I mean at a minimum initiating conversations with a stranger shows some cojones. The apps have taken that major “in your face” element of rejection out of the mix for sure. However, from experience, when you are rolling and confident, then it really doesn’t matter if you are initiating conversations on an app or in a bar to be successful.

The other element of meeting the old fashioned way is putting yourself in situations with potential success. Let’s face it, I’m old, 45, not really old to some, but me hitting the clubs with all the 21-30 year olds is not going to end too well. Sure, if I’m on a date or I’m dating a younger woman, then I’ll go cut it up at a club, but please do not be that old guy at the club! I’m a huge proponent of doing activities that you actually enjoy to meet like minded/interested people. For me, that’s sports – co-ed intramural sports. I like athletic women who are competitive and fun. Here are some other ideas for meeting in person versus the apps:

Shall We Dance?
  • Dance Classes – salsa, square dance or whatever – partner dancing is better since you have to interact with others, but any time you are getting those endorphins going it’s a good thing.
  • Ski/Adventure Club – A friend of mine is pretty involved in a ski club, and she met her long term boyfriend in the group. I think it is a great idea, and they plan all these weekends, which can make for some good meet ups.
  • Farmers Market/Whole Foods – Ok, so this may be a bit farther out there, but I’m a healthy eater and borderline hippie. You have to take some initiative to talk to someone in line or in the produce aisle, but meeting someone who is concerned with their health is a turn on. Plus, something you can share in the short and long term.
  • Church or Religious Center – I’m not particularly religious right now, but faith and spirituality are very important component of a successful relationship – even if you and your person are openly not religious. With that said, most churches, synagogues and mosques have festivals and events to meet people openly and there is always the time after a service to mingle.

On to this week’s story, fair warning, this is a completely self-serving post. Generally, I’m a terrible self-promoter, but the new single, Wegs, is more of an entrepreneur than other iterations.

I went on a date in early December with someone who I shared the blog and Side Action Podcast with, and she in turn told me about her dating experiences. One of the benefits of talking about the blog with dates is getting all those stories about their worst dates. In the conversation, she mentioned how she tried a few non-traditional dating methods like going to a speed dating event and something clicked in me – “I can do those events!!” I mean I’ve been organizing happy hours, watch parties and sports teams for years. So, I have the logistical mind to do it.

Well, the next day, I went to the movies with another friend who I have known for a while. She is also single, and I would be lying if I didn’t find her attractive. The timing for us may not be right now, but no one knows what the future will hold. Anyway, we started talking about my Dating Events idea, and she was like – “Let’s do it together!!” I was super excited to hear that. Over a beverage at the Duke of Perth, we hatched the idea. The idea would be to start with a pre-Valentine’s Day mixer to start then try a Bachelor-Bachelorette Auction, then maybe Speed Dating or something else. We met a few times to figure it out, as I checked out venues.

In the meantime, I do what I do. I told pretty much everyone I knew about the Singles Event in February. In fact, I went skating with some family members and my daughter right before Christmas at the Maggie Daley Skate Ribbon. My uncle has remarried, and his wife has a daughter that is in her 30s, so I invited her to the Event. Well, she works for the Beam Suntory brands, which includes Effen Vodka and Maker’s Mark Bourbon. She said, “Why don’t I sponsor the Event.” I was like, “Really?!?” So, now, my friend and I are doing this Singles Event in February with a major sponsor.

In brainstorming the name of our group and how we wanted to pitch it, my friend and I started riffing on ideas. We started with Mingling Singles, which we found out has a couple of Facebook groups already on. We then figured out if we did M and M Singles, that was open, and M and M standing for Mix and Mingling. We also had the basic tag line of “Drop the App, Meet the Old Fashioned Way!” I loved the concept and the idea of just meeting people in person.

More than A Drink – A Motto

The event is now called – Matchmaker by Marker’s Mark – Meet the “Old Fashioned Way” and will be held on Saturday, February 9th at 7:30 PM at Cindy’s (https://www.chicagoathletichotel.com/restaurants/cindys) which is the rooftop bar at the Chicago Athletic Club, 12 S. Michigan Ave. The event is completely FREE and will feature the Old Fashioned Cocktail made with Maker’s Mark along with a few other signature cocktails. Maker’s Mark will also have a whiskey tasting table to learn more about whisky and bourbon. We will have tasty appetizers and a DJ.

So, what started as a way to help us fellow singles to meet without the apps has turned into a potential venture for me and my friend. It is really fun to get excited about planning these events and all the learning involved with a major sponsor. It’s been a whirlwind.

We will be having a website to sign up on, which is required to attend (hopefully by my post next week), as the capacity for the room is capped. If you are single, then please come. If you are not single, then tell your single friends and if you insist on coming yourself as a coupled person, then be sure to bring a single friend or three with you!

Sometimes being confident and taking initiative leads you to places you never knew you could go. So, don’t be afraid to strike up that next conversation to see where it leads.

Wegs