Sexiest woman at the Retirement Center…

I have really been trying to be more intentional about my dating. Replying back to texts, first messages and making a concentrated effort to thoughtfully swipe. I figure at the ripe age of 37 I need to step up my game.

So when a speed dating opportunity came across my inbox, I knew I had to jump right on it! I even convinced one of my girlfriends to join in with me. (Unlike the last time I went to a speed dating event and took an actual date… what was I thinking?!)

It was an event based out of the city I work out of a couple days a week, so I went straight from there to my work. Walking in I was actually nervous. I have been feeling out of sorts lately with my confidence in general and especially when it comes to dating. So, this event felt more like a personal stretch assignment than before.

I walked into the small bar the event was being held and went straight to my friend at the bar. I quickly ordered a drink and then another. I was going to need a little liquid courage to get through this event!

The host tells us to take our seats. The way the event is run is each person has a number on their name tag. (I was lucky #7) Then you sit at the corresponding table and the guy with the same number sits across from you. You get about 5 minutes per session and then at the end of the session the guy gets up and moves to the next table. You then get about 30 seconds to write any notes and circle “Lets Talk” or “No Thanks”

My first match was actually sitting at the lady’s seat behind me. When the host told us to take our seats this is what happened…

Guy walks over

Me: Hey, don’t sit down yet. I need to take a picture of the empty seat across from me. It’ll make a great photo for my Instagram.

Guy: …

Me: Takes picture… laughs at picture

Guy: Okay, are you ready?

Me: Yes, do you think the placement of this nametag is distracting because of my boobs

Guy: You could place it in the middle of your chest for even more of a distraction

Me: Or just put it on pants on my vagina

This guy was also the only match I made.

The rest of the evening included other classy comments. Let’s just say… ladies and gentlemen my personality was ON and I had 1 too many drinks.

However, as I said before, I did get a date out of it! I know I’m surprised too! The guy said that the boob comment won him over, so typical 😘

Matt* (again never a real name) was a 33 year old lawyer. He was pretty cute and put up with my shenanigans so I was down. I enjoyed that after we matched it was a consistent stream of text messages. I also enjoyed the fact that they mainly focused on logistics. The when and the where of our date. There wasn’t a lot of fluff.

Matt and I met up at a beer and pizza place. I was running early so I grabbed us a table. As I was waiting, I did begin to worry maybe that he thought he had matched with someone else and that he’d be disappointed to see me. But I was lucky that wasn’t the case… the disappointment came later.

I ordered a Bloody Mary and waited for Matt to come.

Matt showed up looking polished with a nice button down shirt and dress pants. I’m more of a jeans gal, but I figured he was just leaving work.

Our conversation started off a little awkward (as most first-ish dates do). We talked lightly about politics (we did not agree) and then I mentioned my child.

He was surprised at how old my daughter was and asked me

Matt: Wait, how old are you?

Me: 36.

Matt: Okay that’s not too bad. You look good for that age. I thought maybe late 20s early 30s.

He then went into how I wasn’t within the age range of the speed dating event, but it was okay neither was he. Apparently he believed it was up to age 32.

I am not someone that is looking to skirt the rules of something as holy as a speed dating event, so I showed him my text messages with the coordinator stating otherwise. He wasn’t convinced.

That conversation didn’t sit right with me, but we continued on to other topics. Our work, family life and sports.

I realized he wasn’t a fan of my age, but I still felt the need to poke the bear a little more.

Me: Actually I have to tell you, I am turning 37 next week. Tuesday to be exact.

His face turned again.

Guy: What are you looking for?

Me: Well eventually to get married.

I know this isn’t a popular first date answer and puts a lot of pressure out there. However, I’m done with dating guys afraid of commitment. I’m not looking to get married tomorrow or with the wrong one. There are a lot of steps to complete first.

Matt’s face turned again. I ignored it and we chatted a little bit more. I should have addressed the elderly elephant in the room, with a good old fashioned “Jill speech”… but honestly I’m a little self conscious about my age and dating. Not because I am ashamed of my growth (I’m proud of that) but my age does put natural time-limits on the progression of dating for anyone that may want children. I’m open to it but it’s a much shorter window than when I was 33.

We continued to chat for about 10 more minutes and then Matt said…

Matt: I’ve got to be honest, I’m not looking to marry a 37 year old.

His exact phrasing and yes trying it made me realize how stupid that sounded.

Me: Yeah I could tell

No shit Sherlock

Him: I mean if you’re open to something more short term I think you’re attractive and think we’d have fun.

Not my style so I passed. We ended the date with an awkward walking away and goodbye. I had told him about my blog and podcast so I said I’ll send the links. He told me of a website where I can watch the NFL games for free. We promised to follow up via text and walked away. I don’t believe there was a hug or even a standard high five. It was so awkward my mind went blank.

After the date I had mixed feelings. Believe it or not, I appreciated his honesty. Also, I realized that he wouldn’t have been a match anyway. There were a couple of comments about politics where I totally disagreed on principle.

With all of that, I wasn’t sure why I kept replaying the age comments on the drive home. I called several of my girlfriends to talk about it. I had a realization about 30 miles in that hit me in a weird way because I have my own insecurities. It wasn’t because he was rude. He was direct. I appreciate direct. I was putting this weird vibe on the date and not at myself and working through my own thoughts.

I would love to say I’m so passed it! However dating at 37 is different than 33 and I have to acknowledge that. It also makes me realize how important the time was where I was concerned about Jack. I would love to say I should have moved faster past him but the truth is that was my journey so I needed that time…. I have to be patient to figure out where it will end. Ugh patience my most challenging trait..


  1. I hear you! I’m not looking to get married again at age 49 but I too have noticed a huge shift in dating as I get older. The possibilities are narrowing pretty dramatically now that I’m almost 50.

    I love that meme, though! Cracked me up.

    Liked by 1 person

  2. Love your post! I’m 80 now and have just started a serious relationship with a 67 year old man. He is my neighbor! I’m so glad I never had to navigate the modern dating scene! Keep trying sweetie! There are some good men out there!

    Liked by 1 person

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.