Dear Anon-O-Box: The Black Hole of No Reply


Dear Anon-O-Box, I have been on an online dating site for a couple months now, browsing girls' profiles and messaging a few. A small percentage have replied, and we've been having what I thought were good message conversations going back and forth. But for each exchange, the girl has just failed to reply at some point, ending the conversation. Have they just changed their minds? Did I say something wrong, each time? Are they expecting me to 'double-message' them, to prove that I'm … [Read more...]

5 Dealbreakers You May Be Including in Your First Contact Email


There are plenty of wonderful, meaningful and fascinating things to talk about in an introduction message, your very first contact with some potential love interest, while dating online. There are also topics you don't touch with a ten-foot pole. Fair or not, everyone judges on first impressions, and unlike real life where you can hang around and be stalkerish (not recommended but commonly practiced anyway), you don't get a second chance if that cursor goes to the “delete” button instead of … [Read more...]

Dear Anon-O-Box: What Does A Scam Email Look Like?

Dear Anon-O-Box, I've been lurking your site for a while, and following you on Twitter; I've come to respect your opinion, and would like to hear your thoughts on something I came across.  I created a free account on, and one of the members on there emailed me.  The first contact (on the site) looked like this: Hello Dear, How are you today?,I hope you are having a nice time, as for me am cool and lonely. Am new to this and most of the guys I read from there profile are not … [Read more...]

Hiring New DreamGirls: What You Can Learn From Their Cover Letters

We put out an all-call on April 15th, looking for the best geek girl writers on the web. (And perhaps a gay geek guy!) We weren't sure how many applicants we'd get, so the flood of emails really shocked us! We ended up with a pool of 93 applicants to consider for the article writer positions we have available. 93!! Yikes. ...and y'know what? We found that the mistakes people make in cover letters are the exact same mistakes they repeat when writing first contact emails on online dating … [Read more...]

Why Men Are Online Dating Failures (Short Video)


Amazing video. I love Evan Marc Katz, he's been an inspiration to me from the moment I stepped on the online dating biz scene. This video is 2 minutes of pure gold and a must-watch for single guys and girls. I will add there's another possible reason why that guy hasn't moved forward: he's petrified that you'll reject him. (Still.) I have clients who will exchange several emails with a girl and it's obvious that she's digging him but they'll still be afraid to make the next … [Read more...]

Dear Anon-O-Box: Is “(No Subject)” Worse Than “Hi” For A Dating Email Subject Line?

Dear Anon-O-Box, I know it's important to create a subject line that stands out. I usually don't write the subject until after I've written a good email, because I want the subject to relate to something in the email. But, at times, I've forgotten to put something in the subject before clicking "send". (I don't know why some sites even allow that.) Is it better to just let the email go without the subject, or should I sent a follow-up that says "Whoops! I sent that too quick."? - Quick … [Read more...]

Are You Unwittingly Telling Women They’re On Your Back Burner?


You've heard me explain why winks are a bad idea. And I'm not the only online dating coach that thinks that winks send the wrong message to the very people you're trying to attract. While chatting with a new client who was lamenting his lack of dates, he told me that he emailed about one woman per day and "winked at many more." *facepalm* He clarified later and said that while he did wink at lots of women, he usually went back and emailed them later. How much later? Oh, a few days, maybe a … [Read more...]

10 Reasons Why Your Online Dating Website Is Like A Gym


As part of my #fit4gencon initiative, I joined a local gym. This, of course, has reminded me about online dating.  (There's not much in this world that doesn't remind me of online dating. It's an illness, I tell ya.) Presenting, in no particular order, the 10 reasons why your online dating website is like a gym. 1. There's a free trial, but you gotta give up your personal information, even if it's just to peek in the windows. With the exception of the free sites, most sites require you to … [Read more...]

Dear Anon-O-Box: Dating Emails Questions Extravaganza

The Anon-O-Box has been way more popular than we ever thought it would be! (This is great, so keep the questions flowing!) We are planning on doing an all Anon-O-Box week coming up soon, so if your question hasn't been answered, we're hoping to clean out the box and get 'em all done! Today's Anon-O-Box is going to answer a bunch of questions regarding everyone's favorite topic - dating site emails!  How to write them, what not to write, how to reply in a way that doesn't scare away … [Read more...]

How Would Online Dating Change If You HAD To Write a “No Thanks” Email?

Let's engage in a little fantasy here. (Not that kind of fantasy.  Seriously.) (No, not the kind of fantasy with elves and dragons either.) Let's imagine what online dating would be like if writing a "Thanks, but no thanks" email were a requirement, rather than an option. But first, let's examine the current system and why it can really suck. … [Read more...]