Dating By Wegs: Swim Big or Go Home

So, most of you do not know me personally, but I’ve had a transition this year.  I’m getting divorced a 2nd time, and got back out on the dating market this summer.  As a guy in his 40s and trying to navigate the dating world, a lot of my friends pushed me to blog about my experiences.  The self-proclaimed “Summer of Jim” or “Summer of Wegs” was upon us all, and given that I share a lot of my experiences with people, I did have my fair share of humorous encounters.  Plus, unlike most guys these days, I actually try to use dating as a creative outlet for myself.  I actually enjoy planning interesting and interactive dates.  Living in Chicago, I have unique access to a bevy of cultural, social and sporting events that most people around the country do not.  So, why not take a day a week to catalog some of the high and low lights from this summer and going forward in the fall for everyone’s entertainment.

Dating By Wegs

I will do my best to do posts every Friday on this topic.  I will slowly list out my strategies in dating and lessons from this brave new world before me and singles out there.

Rule #1:  Creativity Usually Works

So, today’s post is simple.  Dating is about trying new things.  In Chicago, there are probably 500,000 singles between 25-45, maybe more, but the point is if you want to differentiate yourself from the rest, then you need to take chances.  I mean anyone can go out with someone for a drink or coffee.  It takes guts and confidence to go outside of the norm.  For me, I really like to look at what is going on in Chicago over the weekend or even during the week.

A few places to get ideas:

• Chicago Tribune – Things to do this weekend (I’m sure your local paper will have something similar) – http://www.chicagotribune.com/redeye/culture/ct-redeye-what-to-do-this-weekend-chicago-20180919-story.html – In Chicago, this is mostly cultural and festival events, but most people stick to their neighborhood or suburb – get out once in a while.
• Thrillist – https://www.thrillist.com/ – Thrillist does a good job with reviews of places if you are looking for a new restaurant or bar including special events at bars like trivia, music, etc.
• Trip Advisor – https://www.tripadvisor.com/ – Sometimes us city dwellers forget that it is fun to be a tourist once in a while.  Trip Advisor is a review site from anything from hotels, restaurants, events, etc.  It’s nice to see what others are saying, but it is even better to remember that the City has more to offer than the local pub.

The other thing every dater needs to do is ask around.  Talk to friends who are single and see what they enjoyed doing.  I’m a big word of mouth guy, and I like to just ask people what they did on a given weekend, and hint – I actually listen!!  For us old guys, we need to talk to younger folks to see where the hip spots are, and that is ok.  Learn from those who are out all the time.  Don’t be afraid to try that cool spot some night either with a friend or a date.

Success Story

                                                    (Not me, but you get the point)

So, here it is what everyone has been reading this for.  What does that title mean – Swim Big or Go Home?

I started on a new app called Hinge this past Sunday.  Frankly, I was having fairly limited success on the other Swipe Apps and Match.com (I’ll do full reviews of all of these another time).  So, a friend of mine told me about Hinge a couple months ago (I listened!).  So, I jumped in.

First a plug for Hinge, Hinge does a nice job of blending the standard Swipe App with photos you can see readily and mixes in personal information in a very digestible format.  Beyond the pics, Hinge asks you 3 or 4 provocative questions meant to stimulate conversation.  Some examples:  “I know the best spot in town for…” “One Thing I’ll Never Do Again” and “Two Truths and a Lie.”  As a member, you can click on either the pics or answers to the questions to start a conversation.  I think this is great, and really allows for creativity by both people.

I was working through profiles and came across a young woman who listed her “Two Truths and a Lie.”  She wrote:  She can swim faster than me, she has a dog named something and she studied French for 7 years.  Ok, so another rule we will go over later is Being Bold but not Rude.  I employed this strategy by writing to her:  “You can’t swim faster than me….”  Jerky, maybe, but bold nonetheless.  Thankfully, she responded in a positive manner.  She accepted my challenge, which resulted in a lot of back and forth banter about how great of swimmer she is.  Now, I’m not a bad swimmer.  I never swam competitively, but I honestly thought I could beat a 5’4″ woman in a short swim.  Regardless, we were conversing in a playful and ribbing manner for a while, and I took it to the Creative level.

I said – “Let’s do this!”  Yes, I challenged her to a Swim Off.  I found an indoor public pool that was open late to accommodate our schedules – thank you Whitney Young HS.  We set the date and it was on!!  Of course, we continued to communicate both over the phone and via text after that.  She is a really cool person, but the whole experience obviously broke the ice or water in this case.

Last night, I showed up right on time half expecting either a ton of people at the pool or that she would just back off.  Nope.  We had the entire pool to ourselves and she was totally game to beat me, badly.  So, after a quick change and shower.  I spoke to the 2 lifeguards on duty about our challenge.  My date was ready for me.  Turns out she swam for a competitive club in Jamaica from age 8-21.  So, it was like her playing basketball or football against me.  We got in the pool, did a short warm up – which was clearly a chance for her to gauge my ability.  We lined up and had the lifeguards say go in a one length free style swim.  I swam with all my might – fast, as smooth as I could.  She beat me by an arm’s length.  I gave her a high five for her efforts.  She was good.

We then tried one more thing.  She did the backstroke as I did free style.  Well, she beat me by a bit more this time.  Very impressive.  Of course, I knew my endurance to swim at all was not going to be good, but it turns out her stroke was backstroke and butterfly.  So, I think she was faster doing backstroke.  I took my losses well.  She said, “What’s Next?”  I said, “Food, I’m hungry.”  So, we hit a nearby popular bar and taco place called Federales – https://federaleschicago.com/.

My date is really awesome.  We had a great, in depth conversation about dating, our careers – as she is in school getting an advanced degree.  She really appreciated that I did the Swim Off and actually followed through.  Yes, she never let down her trash talking, but I like that.  I dropped her off, drove home and hit the pillow exhausted.

What is the moral to this tale?  I took a real chance in doing this.  I mean I’m a pretty confident guy in myself, body, etc., but I don’t think going swimming on a first date has ever been done before.  The truth is she loved it, and it was really fun.  Not everyone is down with competitive activities on any date, let alone first dates, but if you two are competitive, then do it.  That friendly banter really breaks people down.  Plus, the willingness to take a chance out of my comfort zone and the creativity to find the pool late at night won her over.

Hopefully, this will inspire others to get out of the shallow end and jump into the deep end of dating.

Wegs

What are your most creative dating stories?