The Debrief: Accumulated Wisdom from Online Dating

Rowan, 29, lives in a cooperative house in Roxbury. She’s grateful to live with so many people she can ask for advice!

After getting out of a pretty serious relationship, I decided to finally join the world of online dating last summer. Though I had dated people before, there was something particularly intimidating to me about the idea of online dating. I decided to crowd-source advice, which I refined as I went along. Over the course of the summer, I was also surprised to learn how different OkCupid experiences were for women seeking women (like me) than for others, especially in terms of norms around communication and behavior. Here are some tips I’ve accumulated along the way:


Start with a “shadow” profile
I found it particularly intimidating that the first thing I had to do was create a username. How could I do that without seeing anyone else’s first? One friend suggested creating an account that I wouldn’t use in the long run. This took the pressure off coming up with a username and allowed me to see the kinds of names other people had come up with. I could also try out answering questions and figure out the boundaries of what I was comfortable sharing. After a couple of days poking around with this account, I was ready to create the one I would really use.

Answer some questions
You don’t have to answer every question (the question doesn’t show up if you don’t answer it). Some people thought it was worth answering as many questions as possible to create a more accurate match. Someone else thought that if you answered more than 300 questions, you looked like you spent too much time on the site. A third person suggested deleting all of my answers every few months, both because my answers might change and because it might switch up who I’d have a good match with.

Create profile content
It’s worth reflecting on what categories are deal-breakers for you as you’re looking. Answer questions around them, indicate their importance to you and use these categories to search for other matches. Include some activities/ideas of potential dates so that someone who’s interested has an idea about what to suggest or ways to relate. When you’re done, have a friend read it over to make sure it makes sense and accurately represents you.


Determine your goal
Are you trying to meet a long-term partner? Get more dating experience while being open to meeting someone great? Learn about your own boundaries and deal-breakers? Do fun things with new people you haven’t met yet? Even if you’re hoping to meet a special someone, other great things may come out of dating—be open to what you learn about yourself and others.

Keep in mind that match percent might not matter
People have all kinds of different theories about match percent. Some only date people with high percentage matches; others prefer their partners to be a little more different from them.

Send more messages
Not everyone responds to every message, so you’ve got to put yourself out there if you want to meet someone. Comment about something the person wrote about in their profile. Ask an open-ended question. See if you can start a conversation, and then see if it’s one you’d want to continue in person.

Move quickly from messaging to meeting
As stated above, people might be great or horrible at communicating in writing. That doesn’t say anything about how you are in person together.

Set a low bar at first
Have a low bar for who you might go out with on a first date. People might not be great at communicating in writing, and unless your relationship is going to only/mostly be in writing, it’s worth meeting someone in person. Low bar doesn’t mean no bar though. Similarly, people can be really nervous on a first date, so if you’re neutral about a second date, go for it. (But if you’re not interested, you’re not interested.) Set the bar much higher for a third date: Is this person worth getting emotionally invested in? Do I see a possibility in this going somewhere?


Be safe
Meet in a public place, and tell a friend where you’re going.

Keep it quick
When meeting someone online, the first date is really just an opportunity to meet each other in person and see if you click. Friends advised me to keep it short and sweet (“Leave them wanting more!”), suggesting meeting for only 20-30 minutes, an hour or two at the most.

Have an exit strategy
How might you end the date? I’ve heard many stories about marathon dates that should have ended hours before they did, just because people didn’t know how to leave or didn’t feel comfortable stopping. Say thank you, and say goodbye.

Keep it inexpensive
Avoid an expensive first date—you don’t know how much you want to invest in this person yet, and unless you want to keep spending money on expensive dates, you should try to set realistic expectations for your time with this person.

Try staying sober
Because you’re trying to get to know someone new and see if you’re interested in dating each other, which is pretty vulnerable, it can be helpful to avoid alcohol. How are you both able to handle that vulnerability?

Think fast
A friend told me that online dating is like taking the GRE—you get instant results. Be in touch soon after the date with a brief message suggesting whether or not you want to see the person again. Does this seem mutual? What parts of yourself does this person bring out in you? What concerns does it bring up for you? Some people find it helpful to design a numbering system to reflect on what happened. For example, check out how Dorise used a letter grade to assess the date itself, and then a +/- to indicate her interest in a second date.

Pace yourself
Some people think dating should start out hot, “boiling” even, and then come down to a simmer as it continues. Instead of clearing your schedule to spend as much time as possible with a new date, aim for lukewarm: have other friends, hold your previous commitments and keep up with your life. Lukewarm dating might be a way to stay grounded and also get to know each other before getting more deeply involved.

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