Dear Crabby, Should I Try Online Dating Sites…

… It’s holiday party season time. You know what that means? ‘Tis the season to be constantly reminded that I am alone. Always alone. As if I could forget.

Alone at mass…


and at social gatherings.

new year


all alone

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Only I have a dog, so technically I never drink alone.

Judgemental dog

Since I’ve written about online dating in the past that makes me an expert.* And because I am such an expert* people tend to seek out my advice from time to time on the matter.

Here’s an example of the typical correspondence I get from readers on the subject.

dear crabby

Dear Pitifully Single Crescat Sad Lady,

I heard you’ve been on every dating website that’s ever existed. Can you tell me which ones are the best? Do you have any advice or tips you can share with me?

Yours Truly,
Hopelessly Optimistic

What Hopelessly Optimistic failed to ask was if I thought online dating sites where a good idea to begin with.

Before I get into site reviews and tips, the number one thing that each person should ask themselves before joining an online match making service is if they ready to share their life with other people. Like really ready? Beard hair on the sink, toilet seat up, sees you without your makeup ready? Or are they just caught up in the emotional pity party that typical leads up to Valentine’s Day?

Next, I ask the if they are ready to sell themselves online. Because that’s what you’re doing by joining these sites — selling yourself online like just another commodity, to be filtered out of countless other commodities based on search engine results that narrow you down by appearance, education, and personal preferences.

totes adorbs

Michelle Arnold wrote a great post about online dating some time back, and we are in agreement on this idea of “selling” yourself. She writes,

I often wonder why more people don’t find it revolting to market their romantic availability to strangers on the Internet, where their biographical sketches are being assessed and picked through by consumers as if they were of no more importance or value than handmade crafts on Etsy. Perhaps it is a byproduct of our tell-all culture, but not many people seem to understand that “selling yourself,” at least in regards to selling your romantic “availability,” is not admirable. The human person is not a product to be sold, bartered, traded, or marketed—no matter how worthy the cause.

Another important thing I ask is if they have any children. If their answer is yes, then my answer is no. No, you should not be online dating. Not only is this inviting trouble for you, but it could potentially dangerous for your children. Do you really want to risk your children’s safety? More on this later, but it is a very poor idea to casually date when you are responsible for children.

Below are a few questions I usually ask someone who has written me on the subject.

1) Are you a typically happy person?
2) What was going on in your life right before you made the decision to join an online dating site?(ex: a friend’s wedding or engagement, a financial pitfall, any major life events)
3) What specifically do you have to offer another person?
4) What is the main reason you want to start your search?
5) Are you free of other attachments that may prevent you from seeking a spouse?
6) Have you talked with many married people? How many married friends do you have?
7) What’s your spiritual life look like? Maybe your longing is related to ignoring your faith?

After giving proper consideration to the above, Hopelessly Optimistic usually turns into Hopefully Optimistic With Realistic Expectations and the idea of joining an online dating site becomes dramatically less appealing.

See, it’s not about which dating website you use or how polished your online profile looks. It’s about evaluating your level of emotional maturity to see if you’re realistically ready for a serious relationship and not just trying to use people to fell better about yourself.

So while I do personally know people who have met their spouses online, those numbers are significantly lower compared to the people I know who’ve used them with negative results. Because of this I don’t recommend anyone start looking for a serious spouse using dating websites as a resource.

Instead what I recommend is a long, proper internal evaluation of where you are in life, where you want to be, and what you’re willing to do to get there.

*expert – term used loosely and maybe a little inaccurately. Just a little

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