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Advice for Reluctant Online Daters

Last week, my mom texted me a pic of a baby.

It wasn’t a subtle hint.

I was annoyed by her hint for grandkids, but I get where she’s coming from. She wants more people in her world to love unconditionally, which is sweet but also inconsiderate because babies are expensive and scary.

Maybe for you it’s not babies, but dating (equally expensive and scary). You know you should get online-- and you’ve probably tried it before-- but you feel reluctant. You hate the idea that you’ll go on a great date and the girl won’t call you back. You hate the idea of spending a precious weeknight with someone who sneezes through the entire dinner, or comes covered in cat fur.

I get it.

There are a lot of reasons online dating sucks: there are too many people out there, it’s a lot of work, it’s easy to get addicted, it’s a huge time commitment, all the people are ugly, no one will respond to you, no one will get you, you’re moving soon anyway, you should finish your degree first...the list goes on and on.

Here’s the problem: the more weeks you live without dating, the more weeks you’ll be alone. It’s a harsh reality (seriously sucks), but it’s true. Plus, the only way to get better at dating is to keep dating.

Take online dating for what it is: a great option. You may or may not meet a match.

Here are some tips for reluctant online daters:

Remember that online dating isn't a solution

Some people, especially those who struggle to "be cool" on dates, or talk to girls at parties, see online dating as a way out.

Online dating is pretty much the same as any other kind of dating. Once you're off the site, you're dealing with real people. That means you need to be confident, comfortable in your own skin, and ready for love.

People are looking for connections. Online dating is simply a way to find them.

Choose the right dating sites

Tinder, OkCupid,, or something else? There are tons of dating sites. Which one to choose?

Here’s some advice for guys in Boston:

  • You need a mobile app. Get either Tinder, Coffee Meets Bagel, or OkCupid’s mobile app. Everyone is on Tinder, and it helps to know what options are out there. It’s also kind of fun, and allows for instant connection. The problem with Tinder is that many people aren’t looking for serious relationships. If Tinder is too overwhelming, try Coffee Meets Bagel (it sends you one match per day).

  • You need a real dating site, too. Mobile apps aren’t enough. Pair your Tinder addiction with OkCupid or OkCupid’s mobile app is fabulous.

  • Read this article on LifeHacker detailing the different sites. Again, I recommend OkCupid,, and Tinder.
  • You get what you pay for. On sites like OkCupid and PlentyofFish, women are used to THE WORST messages. Like, do you spit or swallow? What’s your favorite sex position? Women that are looking for relationships are willing to pay-- just to get off these terrible sites. I met my boyfriend on OkCupid and he is a stand up guy, get what ya pay for.

Find a woman to read your profile and be brutally honest

I realize guys are reluctant to ask other guys about their online dating profiles. Here’s where women-- your mom, sister-in-law, co-worker, old college friend, or someone else-- can come in handy.

Women have a knack for knowing what works. After all, we’re women, and we’re the ones who check out hundreds of profiles.

The trick is to ask this woman to be brutally honest. Women are really nice. We don’t want to hurt your feelings. That’s sometimes why we tell our friends they look great when we’re actually not sure. Tell her you want to know everything that’s wrong with your profile...and to not hold back.

She will help, I promise.

Decide how much time you’ll spend

People often complain that they join an online dating site and proceed to give their lives away to the art of finding a date. It’s a numbers game-- you have to send out tons of messages before getting a response (statistically, the average is 1 in 6 messages will get a response).

That doesn’t mean you should sit at your computer and spend 4 hours surfing OkCupid.

  • Make a schedule. It sounds lame, but decide to make each Tuesday “message-sending” night, or send only 2 messages per day. Give yourself a limit so you don’t make yourself crazy. And be patient-- if girls aren’t biting at first, keep at it. If you’re still having no luck, re-assess your profile, photos, and messages.
  • Get a distraction-killing web app. If you’re finding yourself checking your dating site as often as your Facebook, get ColdTurkey, which allows you to block certain websites on a schedule.
  • Disable email notifications from your dating site. If you don’t do this, you’ll be tempted to visit every day, all the time. Decide when you’re going to log in. If you’re messaging with someone, check once per day. Not more.

Pick better people to date

If you’re sending out messages like a mofo and no one replies, what’s going on?

Did you know that, as humans, we’re terrible at picking romantic partners? This is bad news when it comes to online dating.

I see tons of guys going for the hottest girls on their dating sites.Just because you and a woman are on the same site doesn’t mean you’ll hit it off, or that you stand a chance.

When messaging someone, ask yourself:

  • Can I imagine this woman hanging out with my friends?
  • On a typical Friday night, is this person doing similar things as I am?
  • Am I attracted to this person purely on a physical level?
  • Does this person seem to share similar values?

If you can’t seem to land a date, ask for help. Ask friends, family, or me (that’s what my job is), to help you pick a few prospects. Imagine they’re setting you up on blind dates.

Date multiple people (if you can)

This is easier said than done, and easier for girls than guys, but a great way to stay sane while dating is to date multiple people at once. Don’t get this twisted-- I don’t recommend that you sleep around or get multiple girlfriends. Instead, keep your options open. Don’t get too hung up one one girl before she’s ready to get hung up on you.

This is especially important for people who become extremely anxious when they meet someone they like.

Take care of your emotional health

Online dating is an extension of who you are. It’s not a solution to singledom, and you won’t be able to get a date unless your emotional health is in tip-top shape. That means a certain amount of self-love, understanding, and adaptation.

Here are some suggestions for building a healthy emotional life:

  • Read some books. Don’t read a phony book written by a pickup artist. Instead, pick up Attached: The New Science of Adult Attachment or Natural: How to Effortlessly Attract the Women You Want. I used to think self-helpy books were bogus, but I’ve actually read a bunch that give new perspectives and are truly helpful.

  • See a therapist. Therapists can help you understand what ruts you’re running into when it comes to dating, and why it might be particularly hard for you.

  • Cultivate friendships. Get out of the house and see people, whether that’s existing friends or family members.

Build an offline life, too

Part of having a healthy emotional life is building a life off the computer. Use your singledom to spend time cultivating new hobbies and interests, especially those that include other people, such as martial arts, kickball leagues, running, cycling, seeing great bands, joining Meetup groups.

If you have a rich life offline, then you’re more likely to meet people in general. Online dating is a way to open yourself up to the world’s possibilities. You need to open up on and off-line to meet the right person.

This rich off-line life will make you extremely attractive to the women you meet online.

Practice talking to girls outside of dating situations

Women are everywhere. Don’t be afraid of them. Talk to them outside of dating situations. Please, I beg you, don’t be creepy! Don't try to pick them up with suave lines. Simply make an effort to talk to women more.

  • Ask a co-worker how her weekend was. Try to sustain the conversation longer than usual.
  • Chat up a girl at a coffee shop. Don’t be creepy. Just make a joke.
  • Make a point to talk to women in appropriate places, such as at parties, bars, and while your kickball team is having an outing.

Stop being reluctant ... and be patient

I can't convince you online dating doesn't suck. In a lot of ways, it does. However, if you're not online dating, what are you doing? How will you meet the love of your life?

Remember, these things take time, so you'll need to be patient. Youre' unlikely to hit it off with your first date. If you keep at it, you'll get somewhere.

Stop being reluctant, and take these tips and get out there.