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 riging 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?

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.

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-

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

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 .

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?

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.