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They say age is nothing but a number. We see it all the time in Hollywood. Hayden Panettiere is having a baby with someone 14 years older than her and J.Lo just broke up with a guy almost 20 years younger! Clearly, age means nothing to them.

I decided to conduct a sort of social experiment. I wanted to go on a date with a guy in his 20’s, a guy in his 30’s and a guy in his 40’s. I chose to stop at 40’s because my father is 56 and wouldn’t have felt comfortable being on a date with someone literally old enough to be my dad. So my thumbs got to work swiping left and right until I managed to narrow it down to three candidates, with about three generations between them. I approached each date looking for specific things that different age groups might do differently, and took tons of mental notes so without further hesitation, let’s take a walk through three decades worth of men.

I thought 26 was a good place to start since it is about my age and I figured I already had that in common with the guy. He worked in sales and said it was his second job since graduating. It wasn’t bad, but it wasn’t great. It just was.

Location: We met at a bar in midtown Toronto because he worked in the East end and I downtown, and it was a central spot for both of us. It was at 9 pm and at a typical pub. We ordered beers and chatted the night away. This spot was my idea. He totally deferred location options to me and I thought this was a safe bet.

Outfit: Jeans, a plain tee, and what looked like men’s Toms. Basic, cute, but not much effort. Generally, what I think a 20 something would wear. Sort of a snooze fest.

Living Situation: At home, with his parents. Owned his own car.

Conversation/Chemistry: Conversation flowed easily and we talked about our time at school, our families, and our hobbies. There were a lot of things we had in common, but mostly superficially. That said, there were times where he talked hanging out with his “buddies” every day and how he went out to party EVER. SINGLE. WEEKEND. Maybe the 20 something male has more energy but I just can’t do the every weekend thing anymore. When I mentioned my engaged friends, he actually bristled and changed the subject.

Final Verdict: A nice guy, but not yet a nice man. He seems to have a lot of growing up to do. There are a lot of guys in their 20’s who are mature and stable, but this guy was not one of them. Had a nice time though, and met a new person.

I am almost 30 (27) so I felt that this date would be a lot like every other date I’ve been on lately, and easy to navigate. I was right. Sexy finance guy, my specialty.

Location: We both work in the financial district downtown, in the same building, so we met for a few glasses of wine at a wine bar attached to our building’s lobby. One thing about us downtown Toronto folks is that we don’t like to travel far to find food and drink.

Outfit: A suit…oh and what a suit it was. That thing fit that guy’s (perfect) body like a glove. Think Harvey Spector. Can someone get me a fan please because I just started sweating. Despite that, every guy in downtown Toronto dresses this way so again, sort of a snooze fest.

Living Situation: Condo downtown, obviously (no, I did not get to see the condo, sadly). No car, but part of a Zipcar program to rent whenever he needs one.

Conversation/Chemistry: The convo flowed really well. We both work in the same industry so talking about finance and the stock market came naturally and it showed me that he was smart, financially savy and had planned for his future; three important qualities I look for in a man. He had a lot of interests, worked out at the same gym as me, and loved to travel. Case in point, I had a lot in common with this guy and really clicked with him. While he seemed to still want to cling on to that youthful, out with the guys lifestyle, he was also open to meeting someone for long term.

Final Verdict: Amazing guy, easy on the eyes, intelligent, and open to the same things I am. We have kept in touch and met for a drink one other time. Jury is still out on where this will go.


The 40’s date. I was nervous, I was anxious, I was a bit concerned that someone might see me. He ran his own consulting business, and described himself as “comfortable and my own boss”.

Location: He chose the spot, but we met near my office first to walk up together. We ended up at a sushi place in Yorkville, a really swanky part of the city. I love sushi, and I love Yorkville, so this was a perfect spot for me. He chose what we ate, with a bit of input from me.

Outfit: This man won the outfit category. He was in dark wash jeans, a black v-neck tee and a beige blazer with black loafers and no socks. Basically, the picture of upscale casual and as if he had just stepped out of a J-Crew catalogue. He even had salt and pepper hair, adding to the sex bomb look. It’s like his clothing said “Yeah I’m over 40, I’m established, I can wear shoes with no socks and get away with it”. Hot. Yum. Not a snooze fest at all.

Living Situation: Owned a house in midtown Toronto (another amazing area), had a BMW. Has white picket fence, needs wife to fancy up the place, pretty much.

Conversation/Chemistry: This guy knew something about everything. He was well travelled, well established in business, and had a wide variety of interests. From the gym, to dragon boat racing, to learning a new language (Spanish), he was the complete package. There were times during the date where conversation would subside and the silence was not awkward. He willingly complimented me and I felt beautiful. While we were walking around Yorkville afterwards, he held my hand. This guy knew romance, and he knew how to treat a woman. He told me he wanted to meet someone to have children with. I respected this and found it very attractive. I found him very attractive.

Final Verdict: Mr. 40-something was wonderful, smart, handsome, charming, BUT, a few years ahead of me in what he wanted. While I do want a husband and children, I want that within the next few (5) years, not next year. His timeline was a bit more pressing than mine and while I loved that he was open and honest about that, it is not something I could offer him. We got along great, and I do hope that we can stay in touch in a mature way.

So what did I learn? Men are all the same at any age, but also very different. I think the biggest difference was 26 and 43, with the 35 year old being the one I felt the most at ease with. I expected this. What I wasn’t expecting was to be so attracted to and interested in the oldest of the three men. He was everything someone thinks about when dating an “older man” and I am so glad I can say I have done it. All in all, it was nice to meet some new people, especially one I would never normally cross paths with.

Have you ever dated or married someone older than you? Is age really just a number? Leave some comments and let us know! 

Written by Cat