The Pros and Cons of Online Dating

Frugal Portland mom and dad

Mom and Dad met before Al Gore invented the internet

I’ve been thinking more and more about online dating.

My lifestyle is one where I wouldn’t necessarily meet someone unless he is working out at my gym, going to my grocery store, or … you know, walking into my house when I’m sitting on the couch in my sweat pants. And if the last one happens, I’m much more likely to hit him with a frying pan than I am to invite him to have a cup of tea.

But at the same time, I’m ready to meet someone.

So, I thought I would do a pro/con list. Hey, if it’s good enough for Ben Franklin, then it’s good enough for me, right?

Pros of Online Dating

  • Everyone who signs up for online dating is single (well, I guess that’s just a working assumption, may not be 100% true!) so there’s no risk of meeting someone awesome who has other obligations
  • I don’t have to put pants on in order to peruse the selection
  • I would get to go on a date sooner than letting serendipity run its course
  • Girls attract a lot of attention on these types of sites, so it would be good for my ego
  • My dating skills are rusty, and this could serve as decent practice
  • There are nice people on the internet (as I noted just the other day!)
  • Online dating is better than not dating (maybe)

Cons of Online Dating (inspired by this post at Dating is for Douchebags)

  • Removes the first several steps of flirtation: the eye contact, the look, the awkward first few sentences, the would you look at that? moments. AKA the really fun beginning parts!
  • Dates start at step three, instead of learning things about another person in a more natural way
  • Treats dating as a commodity where you can sort by hair color, ethnicity, weight, education, job, salary, etc. Things that you shouldn’t really get to pick and choose. We’re people, not shoes!
  • For the pay sites, there is absolutely no incentive to match people up. Non subscribers get a lot of attention, which is an incentive to pull out the credit card. But then it tapers since these site don’t benefit from two subscribers getting in contact.
  • The internet pulls down barriers, and there’s a chance to get flooded with emails from people who would be too scared to make eye contact in real life, let alone strike up a conversation.
  • Online dating is marketing. It’s selling yourself, sending peppy upbeat emails all the time. I’m in marketing, this is what I do for work, and it’s draining enough. Now I have to do it with me as the product?
  • I would have to put pants on, thereby interrupting my very busy life of having my pajamas on by 8pm most nights.
  • When you meet someone on the internet, the assumption is that you’re one out of five, at best. When you bump into someone at the grocery store, you don’t really even think about another person.
  • Similarly, when you meet someone from the internet, there’s something akin to winning early in the night at the casino. Well, that was awesome, let’s see what else is out there! is kind of like, whoa, I just won $250 in my first 15 minutes of blackjack. I am unstoppable! This mentality keeps you from getting close to someone, and it keeps that $250 where it’s safe, in circulation.
  • When you pay for a membership, you commit to something like six months. Unless you want to pay a LOT more for that first month. Let’s say you meet someone amazing offline in day 3 of your online dating membership. Then, you wonder if you can “do better” — this is detrimental thinking. I guess you can force yourself to think of the membership fee as a sunk cost, but that takes a bit of effort.
  • It’s not in the site’s best interest to match you up with someone. They want you to renew. They want you to continue.

The other day, I went to and typed in my ZIP code. I saw a few friendly-looking faces, and then a thing popped up.

“Try it! Just answer a few questions about yourself and who you’re looking for!” the thing chirped. So, I did. That was fun, just like any online survey is fun. It lets you set deal-breakers, which, let me tell you, makes you feel like a really awesome person. Hey, it’s true, smoking is a deal breaker. Sorry!

The next morning, I realized the genius that is

There were eleven emails from Match, using words like wink and smile and email and favorite. Boy did I feel popular!

Clicking any of those brings you to the subscription options.

Of course it does.

Match will tell me, “hey, we found someone for you. Like you, he’s not a smoker, and he likes dogs.”

WOW thanks, Match!

For now, the cons far outweigh the pros.

And now, I’m off to put my pajamas on.

Have you ever tried online dating? Good experience? Bad?


  1. My brother and his wife met on They are very happy. He DID have quite a few dates that were horrid but he kept at it. He is a software engineer for Northrup Grumman and she's an elem. teacher and they are perfect for each other. Make sure your con list is not a list to just talk yourself out of it–you might be missing a great opportunity to meet people.

  2. Online dating seems a bit tough if you ask me. Almost all they guys I talk to aren't really even looking for relationship but rather just a quick one night stand which makes it even worse. I guess to each his/her own.

  3. I've been using online dating sites for years, even Match. They are all full of crap in their claims. Half of the people put up old, flattering pics and just describe themselves as they ultimately wish to be or how others want them to be. And that's both men and women.

    I do disagree about the early stages of dating being lost, though. If anything, it makes it easier by letting you know who possesses certain traits you want/hate beforehand like the smoking or drinking habits, job type (I can't date someone who has night hours at work) , or other tidbits that each site has a place for. There is still going to be that first encounter with the butterflies, but you may simply know a little more going in than if you met someone in a bar.

    Then again, some people believe in love at first sight or falling in love before even meeting which I find to be garbage too :-)

  4. Anne_UGifter says:

    Hahaha. I know of some people who have had a lot of success online. I also know others with crazy stories, I think it's all luck of the draw.

  5. Do it! You have an advantage if you are already working in marketing.

    I've had good experiences with online dating and have been pretty lucky with my matches. No horror stories (maybe I just have very good filters for what I'm looking for). I dated the first guy I started talking to for a little bit, and when that ended, I opened an account on a different site and dated the first guy I started talking to there too! Things are going really well. I can say he's the love of my life, and we're moving in and building a life together! The things that would not have happened if you didn't take the plunge.

  6. First, who redesigned your website? Would you be willing to email me about your experience?

    Second, Greg and I met on the internet over 12 years ago. We just met in a chat room and it was waaaaaaaayyyyyyyyyy before internet dating was cool. However, there isn't a day that goes by that I don't thank God for that chance encounter. We never would have met otherwise and he is truly my soulmate. We are meant to be together.

    I say, give it a try. You might meet some people that you wouldn't have met otherwise. You may even meet someone who you are meant to spend the rest of your life with. And if you do, you may end up being thankful every day for the rest of your life like I am.

    • Frugal Portland says:

      WOW you met on the internet!? In a chat room!?! This I learned today! Also, you flatter me — I just did the redesign myself because I wanted something prettier. It took a few hours, and I felt productive, but I’m not sure I actually accomplished anything!

  7. moneybeagle says:

    In 2000, I dated a girl throughout most of the year that I met via online dating. It was pretty new at the time, so new that we lied about it as we weren't sure how people would react. Now, it's so common that I don't think anybody even thinks twice about it. My wife and I met face-to-face, but a couple of my buddies are happily married to girls that they met online. It works!

  8. John S @ Frugal Rules says:

    I am with Holly, I like the redesign! In regards to online dating I say go for it. I've known several people who've met their future spouses using one and they couldn't be happier. My brother has used Match and has had some good results overall.

  9. Nice redesign of the site!

    If I was still single, I would give a shot. Technology seems to be taking over everything these days, so it may be best to just go with the flow. Besides, while your profile is out there, you could always be working on really getting dates in the real world.

  10. I tried it after a breakup, and it was a MAJOR ego boost. I did end up dating a guy for like 5 months, but it was a total pity date thing, like I didn't really like him but he was super nice and treated me well and I felt like he was the kind of guy I was SUPPOSED to be with, you know? I will say that online dating is more of an ego boost than anything else. But then again, i know of a lot of people who have met through online dating, so i dont know. just approach it with an open mind i guess.

  11. Online dating scares me to death! I have been married for 44 years and thankful this is not my reality. I think you have to put yourself out there to meet people. If i were single I would start with places where I could meet people who are interested in the same things. I would volunteer at museums, every religious organization has a singles group or just attend services. I would take classes such as wine or other personal interests. There are single travel groups or join personal interest clubs/organizations. For me, it may be a cycling club. Don't forget to network with your friends which is how I met my wife. Good Luck.

  12. I met my husband on Plenty of Fish. It was my first time trying online dating. I was a bit skeptical because I use to think online dating was for desparate people. But I must say I absolutely loved it. It's much better than meeting someone at the grocery store and making small talk because you don't want to be rude. Online, you don't even have to respond if you don't like the person.

    Hubby was the fifth guy I went on a date with. One tip I will give is meet the guy sooner than later. My girlfriend gave me that advice. She said sometimes the conversation is great online, through text messages and even over the phone, but when you meet the guy it may be different.

  13. I've always thought online dating was not for me, but I guess you can't argue with results. Eventually I decided that there is virtually no downside, and so it's probably worth a shot. We'll see how it goes…

  14. Canadianbudgetbinder says:

    Many people we know met online and it was a great experience for them. One couple even got married and that was many years ago and they are still happily married. I know there are pros and cons but like anything else people can be whoever they want to be whether you meet them online, a bar, shopping wherever. If it's true love and meant to be then it will be. Great post! Mr.CBB

  15. I have never done online dating,but I'd give it a try. That seems so much easier than getting dressed up to go out and having to put on your sort of game face for meeting new people. I think internet connections go much faster because you can be more open when not face to face at first when you are worried about your hair, clothes, etc. I also like the redesign. Great job.

  16. I'm a teacher and have done my fair share of online dating (ending with marriage to my husband, who I met on eHarmony). I also have four friends/coworkers who met their husbands online. I did have some lousy dates, but met a fair amount of normal, nice guys, too. I had the best luck posting an ad on Craigslist and, of course, with eHarmony (my husband was one of two guys I met on there). I found that was the worst. It seemed like a lot of the guys on there were using it to casually date rather than looking for a serious relationship. Anyway, I recommend it overall, but it can be a little exhausting going on all those dates. :)

  17. I wouldn't dismiss it forever, I know a lot of people who met their partners on sites like and are really happy.
    I met my partner prior to this whole internet dating thing taking off, but if for whatever reason I became single again I'm almost certain that I would give it a try.

  18. I say do it! After all, what have you got to lose? Worst case scenario you end up with a funny story to tell on your blog.
    Although, I have zero experience in this area, as I'm marrying my high school sweet heart (though we DID initially start chatting online because we were both too shy to talk IRL!)

  19. Site looks awesome FYI.

    I have actually known of numerous good experiences from online dating. In fact one of my best friends is getting married in 2013 to a guy she met online. I think there are pros and cons to every dating situation and you just have to be aware of them. I know in person dates definitely have their issues – like the time I ended up back at a guys apartment for three hours when all I could think about is how to leave.

  20. Outerspaceguy says:

    I've been on okc on and off several times, and have met some great people there.

    I think you should do it. Pick a free site, like okcupid, and express yourself into your profile text, knowing that you can simply not respond to anyone. Make sure to include multiple photos that clearly identify which one you are (if you are in a group photo), and if possible, choose photos that are taken from different angles. Have at least one photo that clearly shows you from head to toe. Use recent (< 1 year old) photos of you that were taken with a good/decent actual camera (which is typically NOT your phone's camera).

    If you don't have any recent pics, well, then that is a different problem. Get out and learn how to use the "countdown timer" function on your camera. _Then_ make your profile, showing how independent and outdoorsy you are. :)

    Your photos will get guys to click on your photo, but your text is how you close the sale and actually get them to message you. [If you don't have any text, or you don't have good text, then all you are selling is your photos: expect messages accordingly.] It is okay to direct how you write your text so that guys who you are interested are much more likely to contact you. Make your text interesting or funny, and give that guy an easy topic or two from which to initiate a conversation. Model it after profiles that you like (if you want a starting point), but make your text yours. Keep in mind that seemingly every girl wants a guy who is much taller than she is. Resist the temptation to express that (think of how you'd react to a guy's profile explicitly saying that only women thinner than he is should message him).

    When creating your profile, upload your photos as the last step (if you can). You don't want guys visiting your profile before you are ready to show it off.

    If you see a guy you like, absolutely message him. Your odds of getting a response increase dramatically when you make the first move.

    Otherwise, be creative and have fun with it….

  21. Having read this guest post and your obsession with sitting around in your swears I am convinced we are soul maters.

    • Frugal Portland says:

      THAT is probably my problem! One of my really good friends sometimes comes over in fleece pants. We have a BYOS (bring your own slippers) movie night about once a month.

  22. I think you should give it a chance. You might meet some interesting weirdos. :)
    I'm so glad I'm married.

    • Frugal Portland says:

      You just want more stories! How about this: I’ll let you know where I’m meeting people from the internet and you can come spy on me. 😉

  23. I think I mostly disagree because most of the cons actually apply equally to any other kinds of dating. Example: dating is marketing regardless of where you meet. You still have to market yourself whether you meet online, in the library, at a bar, or wherever. Another example: you are one out of five whether you think about it or not. That isn't specific to online dating at all. Other of your cons I actually think of as pros, such as the breaking down barriers thing. I think it's good that people may contact you online who would be afraid to initiate conversation in person because if the people initiating conversation with you in person were all that great, you probably wouldn't be online to begin with! It's good to branch out.

    Plus, the whole flirting-in-your-underwear thing is pretty nice. MOST bars I go to don't allow that. Usually.

    • Frugal Portland says:

      you are definitely right — it certainly looks like I am talking myself out of dating altogether. perhaps I am just not ready to jump in? perhaps online dating would in fact ease me in to things?

  24. I think I mostly disagree because most of the cons actually apply equally to any other kinds of dating. Example: dating is marketing regardless of where you meet. You still have to market yourself whether you meet online, in the library, at a bar, or wherever. Another example: you are one out of five whether you think about it or not. That isn't specific to online dating at all. Other of your cons I actually think of as pros, such as the breaking down barriers thing. I think it's good that people may contact you online who would be afraid to initiate conversation in person because if the people initiating conversation with you in person were all that great, you probably wouldn't be online to begin with! It's good to branch out.

  25. Pauline @ Reach Financial Independence says:

    I tried it briefly and went out to dinner with a couple of guys but nothing happened, I was too stressed by the whole "I looked for a match online" thing. I did however spend 4 years with a boyfriend that I met on a travel blog, where it was informal and easier for me to talk to people. Maybe your post lands you a new BF in Portland! Your site looks good, congrats!

  26. Digging the new design! The thought of dating kind of exhausts me (glad I am engaged…) I know a lot of bloggers who met their partners through online dating; I guess as with most things in life it's all a bit of a gamble.

  27. Go for it! Brian and I Meet through mutual friends but I have met guys from the internet before and it’s generally been a pleasant experience. Most people feel as shy and awkward as you would.

  28. I met my partner on a dating site for dog lovers called so online dating can and does work fro some people!

  29. I think that OkCupid is a much better way to go. They are free and if you have some sense of what you are looking for it's easy to weed out the freaks. I met my boyfriend there and was so inspired by online dating and how it can help you clarify the picture of the kind of relationship and partner you want I wrote a book on it. MODERN LOVE: The Grownup's Guide to Relationships & Online Dating. You do have to put some effort into it and going in armed knowing what it is you are looking for (and what you aren't looking for) for that matter. I have major issues with the pay sites though.

  30. alwayshungry4 says:

    I agree with giving it a shot – if ever, you meet someone that you might end up being good friends with or who might know other cool people to hang with. I met my bf on Match almost two years ago and what I thought was a "test run" to go back into dating again ended up being a long-term relationship where we're now living together. It can be a chore at times, but at least it gets you out there and hey, a girl's gotta eat! j/k

  31. I'm late to this party but a lot of your "cons" are just plain wrong. It all comes down to how you use it.

    I would never put my hometown, college, major, job or other specific details in my profile – this way first dates are still exciting! There is none of this "start at step 3 business". You still spend the first date doing the boring "getting to know you" interview because we all know the online profile is just a little teaser/summary of your personality and interests. It's not supposed to take the place of a first date.

    The points about paid dating services are probably true and that is why I refuse to use them.

    I don't understand your gambling analogy at all. I also don't know your dating history but, trust me, after going out on numerous dud dates, the last thing you want to do is throw a good one away! Yes, there is a general "could there be someone better?" thought that may pass through your brain and that is why it's called dating! That is why you don't marry the person on your first date. You can go on dates with two guys in the same time period to gauge your interest with each of them. This is dating in general – not specific to online dating.

    "I would have to put pants on" WHAT? That is the whole point of online dating! You don't! Instead of getting yourself gussied up to go out to the bar in hopes that you can 1) find someone attractive 2) catch their attention 3) make a move/get hit on – instead of all that, you can sit on your couch sans pants reading through personality teasers (profiles). You can even send a little flirtatious message – all sans pants! This should be a pro not a con :)

    Last one, whether you like it or not, we already treat dating as a commodity regardless of being online or in-person. Your brain automatically filters out blondes if that's not your thing, or ignores the girl who laughs loud if that's a turn-off for you. Sure, this isn't as obvious as using a search engine, but it is the same thing.

  32. edwardra3 says:

    If you are looking for an honest-to-god, real-life success story of online dating, look no further. I met my wife on the now-defunct Yahoo! Personals.

  33. Francesca says:

    I met my husband on

    I only met nice people and for me it was a success. I think it's six of one and 1/2 a dozen of the other, worth a go, from my point of view, but with some cautions to keep safe. Any other people I dated I met in bars when younger ( don't do that now ) and only disaster ensued! It's a modern alternative anyway, it served me well. Francesca, Australia

  34. Ah well it can't hurt! My friend met her hubby on, but another friend of mine just tried it and said it was a big waste of her time (and $!) I'd love to hear how it goes though. I actually met my hubs on Facebook of all places. True story. :)

  35. I wish I knew about these dating sites when I was young, I think it's good to date many people before you actually tie the knot.

  36. Saccharissa says:

    I met my now husband online, but not at a dating service website. We met in a (non dating) message board. We used to talk a lot online (Skype), at first it was just voice, then we talked with video. Then later on he paid for my plane ticket to go visit him, at first I was nervous, my parents were somewhat concerned about it (they were paranoid because they had just seen that Taken movie with Liam Neeson, lol) but I was determined and visited him, then I met his parents, and later on we got engaged, and then we got married. We've been married for almost 2 years, so I guess that you can meet someone online, even if it's not in a dating site. :)


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