I’M LISTENING, DON’T LOOK AT ME: The Grumpy Introvert’s Advice on Privacy and Dating

Dear Grumpy Introvert,


I’m a very private man in my 50s and a successful entrepreneur. I’ve been divorced for a few years (no rancor, no kids, just grew apart). Now I’m trying to find a lady of substance, someone strong and smart. I live in a small town and don’t have many opportunities to meet new women, so I’m trying online dating for the first time. However, I prefer not to post my photo or reveal too much of a personal nature online. I don’t want my business contacts or neighbors to stumble upon my info. So I’ve been reaching out to attractive women on various dating sites to let them know (respectfully) that I’d rather email them directly than go through the rigmarole of answering ridiculous sex questions and naming my bucket list. But I keep striking out, and it’s very frustrating. The women I’m most interested in either don’t respond or respond saying they don’t feel comfortable giving out their email to someone with no photo and an incomplete profile. I think this is a bit unreasonable as anyone can post a fake picture in these forums and lie as much as they want. I built my business by breaking rules, not following them, and I’m not about to start changing who I am because a dating profile is “supposed to” be a certain way. How can I convince the women who interest me that I’m serious about my intentions and I’m actually a catch?


Discreet but Eager to Meet

Dear Discreet,

It’s your lucky day, pal. The sun is shining, I’m feeling relatively magnanimous, and my editor thinks your letter is interesting. So, I’m going to give you the benefit of the doubt here: I’m going to assume that your intentions are honorable.

But you should know I’m the first to nod grumpily whenever I hear the old adage about that road to hell being paved with good intentions. Good intentions, as my old seventh-grade homeroom teacher used to say, don’t feed the hogs.

Good intentions don’t much feed a love life, either, Discreet.

Let’s start with two simple, if unpleasant, facts about online dating that I exhort you to take to heart:

Fact One: When used in online-dating profiles, “privacy” and “discretion” are surefire code words for “sneaky” and “boundary-busting” and “Affairs R Us” and “I’m most surely steppin’ out on somebody.” My apologies if you didn’t get that memo. OKCupid probably didn’t know the address to your Batcave—

[Ed. Note: Be nice.]


[Ed. Note: Scratch the Batcave.]

Fine. Discreet, just take my word on this stuff, would you?

Fact Two: When someone refuses to post a photo on an online dating profile, the lack thereof positively screams, I’m sketchy. I’ve got bodies in the basement, and yours would look really nice chained to my hot water heater.

[Ed. Note: Oh, dear.]

[GI: These are tough times. Tough times call for tough talk.]

[Ed. Note: Rein it in.]

I’ll cut to the chase. My simple answer to your question is this, Discreet: If you want women to take you seriously online, you have to stop thinking the rules of online dating are for other people. Let me ask you a question myself, Discreet: How many women without photos did you reach out to?

Now, I’m willing to bet that number hovers around, oh, zero. Methinks I smell a whiff of hypocrisy there.

I know you just don’t wanna, but the only way to win a strong, savvy woman’s heart (on- and off-line) is to play by the rules. Take a deep breath, fill out that profile, and post a decent picture of your smiling mug. No sunglasses allowed.

I understand that you’re a private person, Discreet. In fact, I think a great deal of us introverted-leaning souls identify (painfully and intensely) with your reluctance to show your cards in a semi-public online forum. Online dating is a beastly, ghastly thing for introverts—and even for some sensible extroverts—but in this digital age, with community barn-raisings, church potlucks, and arranged marriages in such short supply, those of us seeking love must think outside the box while still playing by some (fair) online safety rules.

How far does your need for privacy go? Forget online dating for a second. Are you sure you’re ready—and willing—to let someone see the real you? Methinks that your extreme reluctance to take a slight risk of someone you know stumbling upon your online pic speaks to a possible larger, stickier, issue.

What do you have to offer a partner if you’re already unwilling to share the most basic details about yourself so someone can get a real sense of you? What actually makes you a catch? So far, all I know about you is that you’re employed and you’ve done okay for yourself. Which makes you equal to a decent percentage of the population. Who are you beyond your go-to labels of “private” and “entrepreneur”?

Really think about these questions, Discreet. I’m not messing around, and the ladies aren’t either. Your honest and open take on yourself matters, and that info is exactly the kind of thing good women want to know straight out of the gate. Forget about what YOU want in a woman, and start thinking about what you have to give.

You built your business by breaking rules. That’s groovy. Has anyone ever told you that building a business is not the best template to use when it comes to forging relationships? I’m telling you now: Business and relationships don’t work by the same rules.

But you didn’t get to be an outstanding entrepreneur by just breaking a lot of rules. I’d venture a guess that—outside of love, maybe—you also possess a modicum of flexibility, good judgment, and the ability to switch gears when one business tactic isn’t working. Are you willing to switch gears to win a shot at meeting someone special?

Because if you’re honestly looking for strong, smart women, it sounds like you’ve already found them: they’re the ones refusing your approach. They’re cautious. They know their limits. They stand up for their boundaries. And that’s smart.

Do you know how bad it is out there for women on dating sites? Take a look at this to get an idea of the hostility and shaming and danger that women face online. Those are real dudes, Discreet, and they are real angry. You may be a harmless-enough chap, but if you really want to be respectful to the women you want to meet, you need to honor the fact that it’s a jungle out there.

I’ve been focusing on the difficulties and very real dating dangers that women face in hopes that you’ll understand better how women feel when a faceless stranger reaches out. But online dating—or any dating, really—is no picnic for straight men either, I know. (My LGBT readers, I don’t presume to know your experience, but I’d love to, so write soon). Now, if you’re still writhing at the thought of completing your dating profile, Discreet, maybe online dating just isn’t for you and never will be. The on-the-ground approach, although also challenging, may actually serve you better. Maybe it’s time to suit up and hit the conference circuit in whatever field your business is in. That guarantees you’ll be meeting like-minded souls, face to face. Community service is another great route for more reserved people to find each other, with no pretense (or ridiculous sex questions) to harsh your mellow.

You tell me, Discreet. What’s your next move? Are you sure you don’t want to give it the old college try for six months? If you surrender to a dating-profile makeover and give a few of these women a better look at who you are and what you have to say, who knows where it might lead.

I really hope you’ll stay in touch. And I hope that you will take some comfort (and find some humor) in learning that you’re not that special. I say that with great benevolence. NONE of us—not the extroverts, not the introverts, not the ambiverts—are that special, and what a relief that is. Because not being special means this big and wonderful secret: nobody really cares that much about what anyone else is up to because each of us is busy worrying about our own messy, hopelessly hopeful hearts—and how to keep them intact. That’s what I think this privacy thing is all about. You say very little about your divorce, Discreet, but I can’t imagine you went through it unscathed. Love is magic, but heartbreak is lousy.

If nothing else, Discreet, I want you to embrace the fact that nobody on this planet enjoys posting their photos on a dating site or having to answer “compatibility” questions like “if your significant other asked you to squeal like a dolphin during sex, would you?” We ALL hate it. And there’s some common ground right there—funny stuff worth talking about on any first date, no matter how you wind up finding that date.

You’re human, buddy. Embrace it.

Grumpily Yours,

The Grumpy Introvert

The Grumpy Introvert (otherwise known as Jennifer Mattern) is smarter than your average border collie, stronger than your morning coffee, and impervious to Comic Sans and all other forms of forced cheer. She has been an annoying know-it-all since the tender age of 8, when she first began correcting her teachers’ misspellings and offering copious amounts of unsolicited advice to her parents.

Have a question for the Grumpy Introvert? Write to her at [email protected]!