View from the Trenches: A Millennial Man on Dating

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Whenever I tell someone I write a blog about dating and relationships, the conversation often turns to this topic. I recently had an opportunity to chat with “Henry,” about his dating experiences as a 31-year-old living in Washington, D.C. What I always find interesting is that men and women of all ages are experiencing many of the same ups and downs as they live the dating life.

Let’s kick back and hear from Henry while enjoying white bean dip with raw veggies. Since it’s a holiday weekend, we’ll splurge with a skinny version of a margarita called La Paloma

I understand you cancelled all of your online dating subscriptions. How long did you try online dating and why did you cancel? What was your biggest frustration with this method?

I tried it off and on for about 4 years with some success. And I cancelled it, because I don’t want to think about dating as often as I can gain access to a website or app. Which could literally be all the time these days. Online dating didn’t frustrate me specifically. Dating frustrates me. And I realized I often don’t get fulfillment from this activity, so why should I focus my limited time and attention on it?

Really, cancelling my dating accounts was all about trying to achieve balance as a person and trying to be happy with just doing my own thing as opposed to trolling for dates 24/7. I still occasionally ask a woman out and the win-loss ratios aren’t any different if you subtract online dating from the equation. The positive in this is that I end up enjoying my own company more and delving into things that interest me. If I eventually connect with someone special, that’s great. If not, I’ve been living a pretty good life regardless.

Did you have a favorite dating site?

I tried at least 5 or 6 sites in some form or another. The ones that worked the best had the most people on them. OkCupid was a favorite.

Would you like to share some examples of rude dating behavior that you have experienced?

Well, being stood up is no fun. I wouldn’t say that it’s common, but it has happened to me several times at this point. Does it hurt my feelings? Sure. But the real insult is less about being rejected and more about someone wasting your time as you stand some place waiting for a person who will never arrive!

Do you see any changes in the dating experience over the last 10 years (advent of technology, changes in social mores, etc.)? 

I wasn’t really dating 10 years ago, because I was moving around too much for work. That said, my idea of what dating was basically came from 90s sitcoms like Friends and Seinfeld. But dating isn’t that anymore, even if there are similarities. The internet, social media, and smartphones have changed (and are changing) our society in general, including dating. For the better? I can’t say for sure. Better than what?

Have you ever broken up with someone by text or email or have you been on the receiving end of this behavior?

I have broken up with someone by email once, but it was an international situation and before Skype existed. I’d apologize now, but we’ve talked numerous times since then and it’s fine. Also, she’s married and doesn’t give a shit about that. Then four years ago on a holiday, I got broken up with by text. Not fun.

What are some “in the wild” ways you have met women? Any ways you plan on trying? 

Those files are classified, top secret, for her eyes only… So, like for me, if I go out with an agenda and I don’t achieve my goal, I feel disappointed. Solution – I just enjoy what I’m doing and go through my regular routine. Home. Work. Gym. Perhaps a party or a bar. I might meet someone at any of those places, but I don’t focus on it.

Is it hard to approach women? How can a woman make it easier for a man to approach her? 

Yes, because women don’t often look like they want to be approached. It’s not just my imagination either. Digging deeper into this, a few female co-workers have told me about how they are approached daily by strangers and it stresses them out. One woman told me she gets asked out every time she leaves the house. So, I don’t know. Generally, when women are into me it is blatantly obvious.

What is your favorite first date venue/activity?

Hmmm… depends on the woman. Gotta adapt. If it leads to making out though, then that’s great for me.

I have gotten a number of emails from younger men on dating sites and I am always suspicious of their intent but a recent exchange with a younger man prompted me to consider that not all of them are out for money or sex. Have you ever dated an older or younger woman? Do you think a significant age difference in a relationship is a good or bad idea?

I don’t know. We’re talking in generalities here. Unfortunately, maturity levels don’t automatically increase with age for some people. I’ve dated older women and younger women. I would say I’m capable of forgetting about the age difference one-on-one. But on several occasions, the women seem like they can get hung up on it like they suddenly just discovered I was five years younger or five years older than them. I’m not sure the reason why. So, being on the same maturity level or the same wavelength in life is probably a better indicator than age by itself. That said, I can see why 20 year olds and 90 year olds don’t often get together, because what would they have in common?

Do you think women have it easier than men in the dating world?

No. Not at all. They have it worse. Because initially they don’t know if a guy is the greatest man in the world or an axe-murderer. Also, they have to deal with online harassment from people they don’t respond to or crazy people or unrequested photographs of dicks. Or all of the above.

Have you figured out exactly what you are looking for in a woman?

I’m of the opinion that being overly specific is counterproductive. Then, you can’t see the forest through the trees. But to show you that I have given it some thought, I believe positive character traits and good communication are necessary foundational things. I can just write out a laundry list of physical and sexual stuff, but that’s more of a wish list than a set of requirements.

In your experience, are men from Venus and women from Mars?

They are very different. But is it nature or is it nurture? I don’t know. Obviously, I like women a lot. I will say that I’ve had several female friends who dated women for a while and they seem to come out of that experience with strong feelings about the pros and cons regarding men. Meaning, they come out of it appreciating guys more.

What do you wish women would tell you?

What they want. But in my experience, a lot of them don’t know what they want or they feel conflicted about things that I can only guess at. I prefer direct communication across the board, if I’m being honest here.

What makes a good girlfriend? 

It’s like that old quote about pornography. I know it when I see it.

How would you define a good relationship? What are some good tests of a relationship?

Well, I can definitely say what makes a bad relationship. So, that’s my measuring stick for relationship tests. How does a person handle anger, disappointment, or differing opinions? Are they patient and committed? Do they follow through on things they say? How do they treat people that there’s no advantage in treating well? How do they react when life is less than perfect? I guess I see a good relationship as good communication, so any couple that doesn’t have that – I don’t know what they have and that’s their problem.

Do you like to chase a woman or have her chase you?

I don’t think this question describes the dating world anymore. If a woman is interested in me, she texts me or she texts me back. If she isn’t interested, she falls off the face of the Earth and is unresponsive. I wouldn’t call that a chase either way. I don’t know what the hell to call it to be honest. They have to invent a verb for that.

First date sex: good or bad idea?

I mean, we’re all adults here. If it feels right, it feels right. I prefer to wait a while, but that’s under the narrowest Bill Clinton definitions of sex. Then again, first date oral sex? Fingering? Imaginative activity of choice? Carpe diem. Definitely making out. Nothing is obligatory though.

Love at first sight – possible? 

Maybe. I don’t know. Could just be something made up in movies though! I’m not against it by any means.

Is DC a good or bad dating city? Can you contrast with any other places you have lived?

From my observations and from what I’ve overheard, dating is just universally frustrating everywhere. I don’t know anyone off the top of my head who just looooves to date.

I’ve lived in smaller towns and cities where there are too few people for a good dating pool, so things are too small and become complicated pretty fast. I thought being in DC would change my view of dating, because there are more people. But everyone I talk to here is dissatisfied. And a few people I know who’ve dated in New York and Chicago say it’s awful. And that’s even more people to choose from (i.e. sift through).

Do you see a range of dating experiences among your friends?

Yeah. Some people can’t be alone. Some don’t seem to date at all. Some married early. Some are just now getting married. Some are divorced. There’s a variety, I would say.

What do you want a potential partner to know about you?

Personal history, true feelings. Not that I would tell them every mundane thing, but being secretive doesn’t seem healthy either. Then if there’s something they really want to know, I guess I might be open to special requests. That’s a joke, I’m open to their requests.

Do you want to get married? What scares you the most about marriage?

Maybe? Parts of it seem like they would be fun. What scares me is that I don’t want to get divorced and it’s hard to imagine marriage being a good idea realistically

Thanks to Henry for sharing his perspective. Until next week, happy dating or not dating.



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