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3 Things That Happen When You Start Dating An Older Man

1. You get to go on better dates.

Or, rather, you get to go on dates, period. I don’t know if it’s because cusp Gen X/Millennials came of age in a pre-Tinder, pre-Netflix-and-chill era, or if we can maybe all hope to one day grow into the wining and dining lifestyle, but dating an older guy was definitely an upgrade in that dating him actually involved, well, dates. Go figure.

When he held doors open for me at Upper West Side restaurants and held my hand as I stumbled out of West Village bars, my dating life suddenly felt much more Carrie Bradshaw and much less college.

Moreover, there were none of the annoying bad dating habits that modern technology seems to have bred in the younger generation. There was no vaguely suggesting we hang out then just never texting me on the day of the tentative plans, no "U up?" texts at 2 a.m., no pointless back and forth about where we should go for dinner. He made plans and he stuck to them. It was mind blowing.

On our first date, he texted to confirm and got there early to get us a spot. When I walked into the bar, he had already ordered a cheese plate for us. It was the most competent thing I had ever witnessed a man do — a realization that led to some serious consideration of just how low I had set the bar for men and to what extent I can blame it on society.

2. You text less.

For as long as I’ve been dating, texting has been the religion of any relationship. How often you text is the barometer for your relationship status and any decrease in frequency, shift in emoji use, or perceived change in tone has always been immediate cause for panic.

When I was seeing Ray, however, texting was never a big deal. We texted back and forth a few times a week to make plans or sometimes to chat about something specific, but our relationship wasn’t defined by a fixed schedule beginning and ending with obligatory good morning and goodnight texts.

For someone who once used to earnestly believe having someone to constantly text was the main point of a relationship, this was initially a strange, daunting concept. And yet, I was surprisingly fine with it.

Turns out your life — and your relationship/situationship/casual but secretly not-so-casual fling — is a lot less stressful when you aren’t constantly waiting for a text and then obsessively mining each one for hidden subtext that he doesn’t like you anymore.

3. You try to use him for networking purposes.

Ray turned out to be an inarguably good-looking guy, but admittedly, the collection of mostly blurry, mostly distant group shots on his Tinder profile wasn’t what got him a first date. Rather, it was the brief Internet stalk that revealed his job. I was actually explicitly forbidden from ever mentioning his real name, position, or place of work in an article pretty early on, but let’s just say the name of the company he worked for is enough to wet the panties of any unpaid editorial intern in New York. Tinder is the new LinkedIn, ladies.

On our first date, I politely pretended to ask where he worked, but I copped to my Internet stalk a few drinks in and joked, but actually not-joked, that he should get me a job. You know, flirting.

To this day, I even have an unsent text drafted in my iPhone notes to the effect of “Heyyy so I know last time we saw each other I told you I loved you then cried myself to sleep in your bed, but is there any chance you’d be willing to pass my resume along to anyone in HR?”

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Jennifer B. Alcantar

Jennifer B. Alcantar

Relationship Coach

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