Online Dating Workshop



If you work at a public library, you probably answer lots of digital literacy questions: how to change the margins in Word, how to apply for a job online. At Darien Library, we noticed that quite a few people were quietly working on their dating profiles, but they were shy about asking for help. We wanted to create a program where people could ask questions and share their concerns in a safe environment.

While the workshop is open to everyone, it is particularly popular with middle-aged or older adults who are re-entering the dating scene after a breakup.

Advanced Planning

Swipe left, swipe right, wink, create a profile, send a message or two. Basically, research and draw upon your experience (good and bad) of online dating to help others. 


We treated this event as we do all our events, in terms of marketing. The class was included in our weekly events email, on our website, and we did a few social media plugs. One of our local papers picked up the event and ran a story on it where I say some really embarrassing things about getting brunch with my girlfriends to talk online dating.

Day-of-event Activity

Finish your slide deck and notes, pump yourself up, get ready to talk online dating.

Program Execution

This class is structured in four parts:

Overview of different online dating sites/apps. There’s an online dating site for everyone! I always start by mentioning the wide breadth of sites (see image), which always gets a few laughs and calms everyone down. We then take a deeper dive into, OkCupid, Plenty of Fish, Tinder and How About We. In my experience, these have been what our community members are using, but your community might date differently!

Tips and tricks for how to create an attractive profile and send an engaging message. This part of the program is part best practices and part motivational speech. I always use the metaphor that talking about yourself in an online dating profile is a lot like writing a resume — and both suck. I encourage people to talk positively about themselves, speak in stories instead of empty adjectives (saying you like to spend Saturday mornings doing the crossword is a lot more impactful than saying you’re intelligent), and to be confident. Like a resume, I always push people to have a friend look over their dating profile. Our loved ones often have a better idea of who we are! Seems silly to mention, but if you’ve ever online dated you know this is important: when talking about creating the perfect message, I stress that correct spelling and grammar are crucial and to not mention someone’s body or the way they look.

Online and offline safety. In 2014, the FBI reported that people who go online to find romance were at the top of the list of Internet fraud victims. Women over the age of 40 made up 70 percent of the cases. Online dating scams cost their victims an average of $14,000.

These two facts always get people’s attention. I begin by stressing that you should never, under any circumstances, divulge personal information such as credit cards, Social Security numbers or bank information. I also share a list of red flags to look out for when communicating with someone. Beware if the person:

  • Quickly asks to talk or chat on an outside email or messaging service
  • Claims to be from United States but is currently traveling, living or working abroad
  • Asks you for money
  • Vanishes mysteriously from the site, then reappears under a different name
  • Talks about "destiny" or "fate" 
  • Claims to be recently widowed
  • Asks for your address under the guise of sending flowers or gifts
  • Makes an inordinate amount of grammar and/or spelling errors
  • Sends you emails containing strange links to third-party websites

When taking the jump to meet offline, I offer these tips and tricks:

  • Do a Google and Facebook search first
  • Share everything you know about this person with at least one close friend
  • Plan to meet at a public, well-lit place. Share where you are going with a friend.
  • Have an exit strategy. When making plans, say that you have another event at 8 p.m. If the date is going well, say that you’ve decided you don’t want to leave yet! Also, the “I have a family emergency” excuse will always work.

We end our program with a big shift away from the scary stuff: Photos. I spend a bit of time talking about the “medium shot”: a photo that gives a good sense of a person’s body, while also being relatively close on the face. We talk about having at least one “hobby” picture that shows an interest (hiking, knitting, traveling, etc.) as well as having a minimum of three pictures. Finally, we end our event with a makeshift photobooth to take attendees’ profile pictures! All we did was use a camera we had in house, snapped a few pictures in nice lighting, and then emailed them to the individual patrons the following day.


Set the tone early on. Patrons are going to come in nervous and giggly as all get-out. If you create a safe space where patrons are encouraged to ask any sort of question, and treat the subject of online dating with lightness and humor, it will help remove some of the initial awkwardness.

People value discretion when attending an event like this. We’ve hosted the class two times now and haven’t taken registration. I have a hunch taking names and contact information would turn people off. My colleagues have stories of patrons coming to the Welcome Desk to ask for directions and, instead of asking where the class is out loud, will write it down on a piece of paper. After my formal presentation, I always mention that I’m going to hang around and take any other questions that people may have. Folks will always come up and ask any questions they may have not felt comfortable asking in front of the group.

Of course, I have to end by sharing a story. A few months ago, a patron asked one my colleagues at the Welcome Desk if she could speak with me. I went down, and we had this conversation: “Mallory, I’m not sure if you remember me, but I attended your online dating class a few months ago. I went home, created a profile, and well ... this is Jack.” Nothing could have made me happier.


Supporting Materials

Slideshow Images