5 Ways Not To Be A Boring Date

Lessons from dating the most boring man alive.

In my younger days, I read Seventeen and YM magazines. Because they were ever so progressive, they provided dating tips for teenage girls. One gem repeated in every issue: don’t talk about yourself and make sure to ask him questions.

Because it’s never too early to make sure men know that their needs and interests are all that matter.

I’ve kept this wisdom in my back pocket throughout my dating endeavors. It’s worked in my favor. I can make anything sound fun and exciting. “Wait, you actually watch paint dry all day? That’s crazy! Do you have to use specialized tools for that? I bet people tell you all the time you’ve got a great eye for detail, that’s a rare trait in people these days. What’s the most dramatic color change from wet to dry?”

I’m a pro at making any date fun, even if I suspect the guy is gay or he can’t keep an erection longer than 10 seconds. Or so I thought. After a short but tumultuous relationship with Vance, I vowed to be with someone mellow.

Cue Rod the Patent Attorney. Relatively good-looking, an ultra pale dude with thick hair styled straight out of the nineties. Was a former Mormon straight out of Utah. After a few weeks of dating, I’m tapping out. He’s the human equivalent of prison solitary confinement. One more date and I’ll start drawing birds at the dinner table out of feces.

Gentlemen, here is your guide on how to not bore a woman into oblivion.

1. Invade her personal space bubble.

On every date, Rod kept a bizarre distance between us. He is the first date I’ve been on where the guy didn’t try to sit close to me in some way. Usually, guys want to be close enough to let their pheromones ooze your way.

Sitting side by side when meeting someone makes it less confrontational. With Rod always sitting across from me with a table dividing us, it felt more like interviews than flirty, sexy interactions.

The best dates I’ve had occur when we’re within close proximity to each other. An easy way to accomplish this is by sitting at a restaurant bar. The seats usually swivel (or it’s easy to shift directions) so there’s dynamic movement between you and your date. You’re forced to sit closer together which allows for the natural arm or leg touching.

On our last date, I instructed Rod to sit next to me. He reacted like I suggested we snort cocaine at the table. Dude was baffled but acquiesced.

Don’t turn your date into an interview. Actively go out of your way to become part of her personal space bubble.

2. Speak louder.

Remember during the pandemic when no one was around? There wasn’t background noise when you hastily ran through Costco and Home Depot. Those were good times.

As someone who works from home, I admit that I’m still getting accustomed to hearing mobs of humans chattering. It gets loud.

Rod speaks at a level a few notches above a whisper. It’s not that he can’t speak louder. He operates at a comatose frequency. Add to that his sitting across from me and I feel like Mr. Magoo straining to hear.

His lack of vocal excitement, the volume to indicate interest in things, and his almost monotone voice make me feel like I’m watching an old-fashioned documentary.

Have you ever seen someone amp up a crowd by whispering? No. It’s done with energy. It’s done with volume. Don’t be all up in her ear screaming. But audibly demonstrate you’re a hot-blooded male if you don’t want her tuning out.

3. Elaborate a little.

I’m not advocating that anyone prattle off for hours while on a date. Ain’t no one got time for that.

Rod does the opposite. He gives short replies which force me to drill with questions, making me feel like I’m interviewing or interrogating him. It doesn’t make for a fun back-and-forth exchange.

When grabbing drinks at a Tiki-themed bar, Rod mentions to the bartender about his Mormon Mission time in Hawaii (talk about winning the religious jackpot). I asked questions about what he did, where he stayed, how long he was there, and a dozen other questions about the experience.

It wasn’t a negative experience. He enjoyed it. To him, it was like I was asking about toothpaste. This was a topic I very clearly wanted to know more about. Instead of using it as an opportunity to open up, it forced me to pry.

If I don’t ask questions about him, the only other options are for me to prattle on talking or absolute silence. And there have been loads of awkward silence.

When your date seems interested in something about you, even if it seems benign, open up and talk about it.

4. Don’t be funny if you’re not.

I am, admittedly, a comedy snob. I’m not a basic bitch who goes for Big Bang Theory. I’m of the What We Do In The Shadows variety.

Serious guys are the worst. I don’t mean “serious” like “intense murderer”. I mean it like, “chill with a slight smile but nothing else”. That’s Rod’s personality.

I accept that in most interactions, I’m the sarcastic one infusing wit and humor to offset the situation. I’m generally okay with that if it results in a fun time.

In over a month of dating, Rod made me laugh once. Once. Homeboy must be a blast at parties.

He asked me on our last date about an incident at my job. My company is under fire for treating women like garbage and he asked about a few news articles. The conversation was serious. The theme was getting treated seriously and with respect as a woman at my job.

I recalled to Rod about a boss who tried to demotivate me by telling me our VP (who was always professional and never once stepped out of line) was only interested in my work because he had the hots for me. My boss thought so little of me that he pushed the narrative that only someone physically into me would like my work.

Rod turns and says, “oh, your ‘work’” with the bunny ears motion. I’m expressing to the guy that my boss was disqualifying my job and Rod jumped in to support that claim.

He thought he was being funny. If he were all-around hilarious, he’d get a pass because that might be his default mode. Instead, he made assumptions based on my looks to knock my professional ability.

I paused and replied, “no, I mean my actual work. This VP saw the value in my position and how it helped the team.”

If you’re not a funny man, don’t step out of line. If you do, piggyback off jokes told by those around you. Don’t make it awkward.

5. Act like you’re having fun.

I invited Rod to a classic arcade warehouse. The first floor has little food shops and bars. The second floor is stacked full of vintage video games and pinball machines. There’s even a glowing bar with cutesy pop-culture names for drinks.

The place is fun. A total Gen X version of Vegas (because we are too old and tired to give a shit about actual Vegas).

First, Rod wanted to scope out all the food options. Then he wanted to scope all the drink options. We endlessly waffled between both floors while I repeated, “I’m good with anything. Really. Anything sounds good.”

We drank fun drinks with umbrellas in them. The owner of the bar gave us free shots that glowed and probably kickstarted my inevitable colon cancer. We shot zombies. I watched him play his favorite childhood game (some Asteroids knock-off). We played pinball with a 1970s Dolly Parton looming over us.

And yet, I was bored. I didn’t want to be bored. I certainly tried to have fun and the alcohol helped. When Rod scored a point, I hollered. When we played pinball, I laughed when Stranger Thing’s Demogorgon popped out to smack the ball. I shared my drinks and food to increase his experience.

Rod enjoyed himself. But his enthusiasm matched a stroll in the park.

It doesn’t make a woman want to sleep with you if you don’t show your pulse races with excitement. Get competitive. Get loud. Laugh often. Grab her and pull her close when she’s giggling.

Clearly, Rod has the personality of a wet bag of flour. I gave it a shot and tried my best, thinking that I needed to veer in the complete opposite of loud and gregarious Vance.

I went a little too extreme the other way. I met the most boring man alive