Stay Classy, ‘SexyDude’

A dating-blog expert unravels the web’s laws of attraction.

Joanna Rothman '97
Mike Lovett
Joanna Rothman '97

I’ve been dating for 25 years, and I used to have a not-so-secret fear that my last healthy relationship happened while I was a student at Brandeis.

As the majority of my close friends married and started families, I’ve remained single, on a seemingly endless search for “the one.” I’ve tried everything to find him — speed dating, matchmaking, setups, online dating, smoke signals.

Then a silver lining emerged. I realized that the more I dated, the more friends and family wanted to live vicariously through my experiences. So in January 2013, I launched as a tongue-in-cheek blog for sharing my life as a serial dater.

Over the past year and a half, SingleSassy has developed a loyal following and was even selected as one of the top 10 dating blogs by It also led to my role as a founding blogger for Singles Warehouse, a U.K.-based online dating magazine.

Most recently, I began teaching a course called “Writing Your Online Dating Profile.” The class covers everything from selecting your username, creating a killer profile, crafting your initial email, even prepping for your first date.

Whether you’re a recent divorcée, a busy businessperson or just ready to give the dating scene another try, these tips should help you get started on your journey toward finding true love (or, at least, a date for Saturday night).

Find the right online dating site.

Start with a site that charges for its services, such as Match, JDate or eHarmony. Though OkCupid and PlentyofFish are very popular, you have to weed through a lot of spam to get to the serious daters. People who pay for online dating tend to take it more seriously. There are also a lot of great sites for like-minded daters, such as SingleParentMeet or GreenSingles.

Keep usernames classy.

Your username is the first touch point. Choose something original that reflects your personality. For example, I’ve used the username “Loves2Travel2Europe.” Pretty much says it all, now, doesn’t it? Your username should reflect positivity, and it shouldn’t be overtly sexual. Skip “Crazy4U” or “BostonLuva.”

Photo finish: Make a great impression.

In general, you’ll want to upload a face shot and a full body shot. Men often make the mistake of including shirtless photos, and women often include duck-faced selfies. Take my advice: No one wants to see those. Use photos taken in a natural setting when you were feeling your best.

Write smart, part 1: The do’s and don’ts of your profile.

Be your authentic self: positive and honest. Write your profile on a day you’re feeling good about yourself. Be specific about your hobbies and interests. Instead of writing that you enjoy “travel,” mention a recent trip you’ve taken — “I just zip-lined through the Costa Rican rain forest.” You’re more likely to attract the attention of someone who has done the same, or who wants to hear more. Like a TV show? Mention why. It’s a great conversation starter.

Write smart, part 2: Emails that are more than just “hello.”

Since your profile has conversation starters in it, look for other profiles that do, too. Instead of writing a simple “Hello, I like your profile” email to the prospects who interest you, mention something in their profile that drew you to them. If they’re intrigued, they’re more likely to respond. Send out lots of emails at first. It takes a while to get the hang of online dating, and this approach will maximize the number of responses you get.

Plan the first date.

Setting up a first date can be wonderful and nerve-racking all at the same time. Meet somewhere public, and let a friend know where you’ll be. Coffee or drinks are perfect for a first date. Dinner makes a great second date. Did your date mention a favorite place? If you both like museums, plan to meet one evening at a local art museum. If you love the outdoors, meet for a bike ride or a walk. Though dates don’t have to be fancy or cost a lot, a little planning goes far. Think beyond the “McStarbucks” date.

And there you go. The hope is that this date leads to a second, a third, a fourth and so on. Soon you’ll be engaged, and your mother will be plotzing. Invite me to the wedding, will you? It’ll make a great chapter in that book I hope to write soon.

I leave you with this final thought. To all of you Jewish mothers with eligible sons, please remember that I’m single, sassy and, most important, available.

Joanna Rothman, who lives in Watertown, Mass., is a fundraiser for a Boston-based nonprofit. Her favorite first dates include a visit to the Museum of Fine Arts, Boston.

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