Quick & Dirty Guide to Online Dating


This week I was asked by one of my roommates to send some online dating tips to her little brother who had recently joined the fray.  I have used online dating on and off for about 9 years and, in writing my email, I realized that the way I date online now is much different than how I started.  It certainly would have been nice to have some of these bits o’ advice when I was starting.  So I’ve decided to share some of these with you nice people.  As with all things subjective, I’m sure my experience will not mirror everyone’s but these concepts certainly worked for me!

So here you have it,  my far-from-comprehensive, in no particular order Quick & Dirty Guide to Online Dating

  • You always want to spend a little time on your first message to someone.  Be sure to reference things you liked in theirprofile to let them know you liked them beyond their hawt photo.  Don’t worry about coming on too strong – you want to seem really interested.  On the other hand, you don’t want to spend forever on an email.  Just put a some thought into it beyond ‘You’re cute.  Let’s grab a drink.’ 
  • Some will disagree on this, but I will never date anyone who doesn’t include 2-3 photos of themselves.  Likewise, I’m always willing to send photos of myself.
  • As far as messaging twice, I generally wouldn’t.  If you’ve done a good job on your first email there’s no need to write again.  They’ll write if they’re interested.  Most people don’t say ‘No thank you,’ if they’re not interested, which can be frustrating but seems to be how it goes.  A couple of times I’ve had guys write again and it hasn’t really bothered me, but generally the reason I didn’t write them is because I wasn’t interested.  Some people do like to be pursued though so if it’s been a week and no response, there’s probably no harm in a follow-up.  
  • Don’t spend too much time emailing with someone online – generally one email each & then asking on a date is best.  This is mainly because you can have great online chemistry and none in person so you want to get to the date part as quickly as possible before you waste a lot of time emailing.  I wrote back & forth for 3 weeks with my first online date- then phone calls, & when we met, the chemistry was SO not there. 
  • Happy hour dates are best.  You don’t want to plan a whole big evening together because you may realize in the first 30 minutes that you’re not really into them.  I used to say I had plans later in the evening and then I ‘cancelled’ them if I was having a good time but now I think you can just be honest about wanting a quick date to see if the chemistry is there or not.  I like a really quirky, fun, well-planned date but maybe save it for the 2nd date when you know the chemistry is there.
  • If you enjoy the date, let them know at the end that you’d like to see them again.  Follow-up with an email the next day.
  • Message lots of people.  Don’t get hung up on one person you find.  Online dating works best when you put a lot of feelers out there.  Also, open yourself up to going out with some people you might not be immediately excited by (not totally unexcited by but folks that seem like maybes).  It’s good experience and I’ve sometimes been really surprised that someone was a lot more articulate, interesting & attractive in person.
  • Have a few people go over your profile with you & make suggestions.  Sometimes we’re not always the most skilled at presenting the best parts of us.  Make sure it shows your personality.  Make it funny & quirky rather than just saying “I’m funny & quirky” (although it’s good to say it too).  Also, make sure you’ve got good pictures, and get a few opinions about this too. 
  • Get used to rejection.  The wonderful part of online dating is that you have access to a lot more opportunities to date than you’d normally have.  Along with this, you’re going to experience a fair amount of people with whom you are not a good fit.  Try to think about dating as a chemistry/fit thing rather than a ‘they didn’t like me therefore I must not be good enough, smart enough, etc.’.  The truth is that there will be people you have mutual chemistry with and people you don’t.  You can make sure you’re presenting the good parts of you, of course, which helps, but basically there’s little to do to change the fact that some people will have the hots for you and some will not (and vice versa!).
  • If it’s only one date, emailed rejections are ok.  There’s no need to tell the person at the end of the date that it wasn’t a good fit (although some people do).  I think it’s best, if you’re not interested, to email the next day & say nice things about them but that it wasn’t a good fit chemistry-wise.  If you have gone on more than one date, or have had sex, a phone call is more appropriate.
  • Limit the percentage of your life you spend online dating.  Especially when you’re getting started, it can be exciting and you might be tempted to spend too much of your free time engaged in browsing, writing, and going on dates.  Set aside 1-2 days a week to go on first dates. 
  • If you find yourself wanting to go on follow-up dates with multiple people, that’s great, but make sure you stay connected with the other parts of your life- friends, hobbies, alone time.  This is what will help make dating a reasonable part of your life rather than all-consuming and will likely make you a healthier and more interesting person to date!

So that’s it for now.  As many of you know, I have recently started writing a book on dating, exploring why we make poor dating choices and how we can begin dating in healthier ways.  I’ll probably have a short piece regarding onlinedating in the book, so any ideas or thoughts about what I’ve written here are welcome!


2 responses to “Quick & Dirty Guide to Online Dating

  1. Thanks for the pointers. Just signed up for online dating site today. I’ve tried Match and Chemistry before but had no success and got frustrated. I’m going to give it another go though. I think these will help me out. When do you expect to finish the book?

  2. I agree with everything you’ve said – especially the quick meet and greet. Nothing is worse than exchanging lots of great emails, only to find that in person, there’s no magic, or worse yet, that someone has mis-represented themselves.

    To add to your list:

    Be as honest as you can be about yourself, while painting yourself in a positive light. Lying about your age, height, weight, occupation — or worse yet, your desire (or not) for kids or a permanent (or not) relationship can derail things early on in the process.

    You will get found out if you meet people, so exaggerating too much one way or another will be bad — and you won’t meet people who appreciate you for the person *you* are.

    There’s also some etiquette that makes the process smoother. Even if you’re not interested, a simple “not interested” generic reply that most services allow provides a chance to move on to other things. It will also prevent you from getting multiple messages from the same person.

    As well, if you meet someone in person and you’re not interested – let the person know explicitly either in person or via email. It’s freeing for you and for the other person.

    Glad to hear you’re writing a book – it’s sure to be good stuff!

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