Dating in the modern age – do the old rules apply?

I haven’t dated in 13 years and 13 years ago I got lucky.

13 years ago I had just finished taking a 3 year break after ending a long term relationship when I met my late husband (of almost 12 years) on my first try.  So, really, I could say it’s been almost 20 years since I’ve actually “dated”. (WOW!!!)

The landscape has changed dramatically.  20 years ago no one admitted they met someone online.  Now internet dating is the norm.  But here I am….socially awkward, and these days I live in a small town where the pickings are mighty slim – how else do I expect to meet someone?  So, I thought “what the hell” and decided to go ahead and put that cheeky profile I created online.

I chose two sites: and Plenty of Fish.  I wasn’t sure what to expect and didn’t want to have any expectations at all, but of course it’s human nature to have expectations of some sort, right?  As I read other people’s profiles, I started to ask myself: what do I want from this experience?  One of the things I appreciate about the POF site is that they give you intention categories to choose from:  nothing serious, friends, casual dating, relationship, marriage, etc.

I think I know what I’m looking to gain from this:  I want a “relationship”, not a one-night stand. It’s not that I’m opposed to casual sex, but it’s not my style.  That being said, I am a sexual being, as we all are, and I don’t expect to wait months and have a firm commitment and true love before I have sex.  But if I do take the sex step, I want to have some faith it’s not a one-time thing.   That’s reasonable, right?  I’m just really inexperienced at weeding out the ones who have casual intent and this is my big stumbling block.

Once I posted my profile and perused my options of potential matches, I found myself wondering: “so what now?”  I was amazed how many men say things like: “no drama, no games” or “I want to meet, not into endless texting” or “serious inquiries only”.  My initial reaction was “great!”  I’ve had a variety of interactions already (more than I ever would have expected, honestly) and have discovered that the very men who say they don’t want drama and games are the very ones who are prone to those behaviours themselves!

But there also do seem to be a few good men out there.  In addition to some bad interactions, I’ve already had some great ones too. However, I am a bit of a social idiot, I know this.  This added layer of anonymity the internet and/or messaging provides leaves me open to missing the social cues I rely on to decode other people’s intentions.  Layer onto that my anxiety with new people and it makes this whole dating thing a giant pain in the ass.  The truth is I’m kind of an old fashioned girl and although I believe in equality, I prefer to be chased, not the chaser.  My current conundrum is making sure I come off as neither needy nor indifferent.  I have one man I’d like to show real interest for, but I’m terrified of seeming clingy and scaring him away.

There seems to be a new ettiquette that I am wholly ignorant of and that’s scary.  I want to avoid making any faux pas that scare away the seemingly great one but I’m also scared of being “too nice” and unintentionally giving false hope to someone who doesn’t stand a chance.

When does interested cross the line into appearing desperate?  When does flattery cross the line to creepy?  How do you deliver rejection without being a jerk? How do you take rejection gracefully? Is it possible to figure out if someone has serious intent rather than a casual one?  How “real” are people really being on these sites?

So here is a list of questions I’ve found myself pondering and I’m wondering if I can get some feedback from you:

  • who should make the first contact?
  • there are flirt or message options: if I do choose to make first contact….what’s the better way to do it?
  • do you stick to messaging through the site or do you share your phone number for texting/phone calls?
  • how much contact is too much?
  • is it better to be bold and say all the things I’m thinking or better allow my shyness to come through and keep some thoughts to myself?
  • why does every guy want to send me a picture of his junk??
  • you’ve got some chemistry and are interested in going further: do you come right out and ask a guy’s “intentions” or is that just plain old fashioned?
  • what do you do/say when there’s just no chance you’d ever meet this guy?
  • do you stop talking to other men or hide your profile once you’ve found good chemistry with one? it’s my inclination to do this, but what’s the norm and should I be expecting the same of who I’m talking with?
  • I’m usually the opposite of talkative about sex, but I’m willing to open up a little more than I have in the past.  But it seems everyone wants to talk sex: how casually should one treat these conversations?
  • if they move onto questions of a sexual nature before you meet, is this a sign that all they want is sex?
  • in this day and age is it expected that you’ll have sex sooner rather than later?
  • safety first, yes, but what constitutes paranoia?
  • how long do you communicate before you meet in person?
  • okay, you’ve decided to meet and you thought the chemistry was as good in person as it was while talking:  how long afterward should you wait for follow up contact before you accept “he’s just not that into you”
  • okay, you’ve decided to meet and you thought the chemistry was as good in person as it was while talking:  do you make the first contact after the meeting and if so, how long do you wait?
  • if a guy hides his profile or removes his pictures after you’ve met him, is this a signal to you that he’s taking you seriously or is he actually hiding from you?

I’ve got other questions floating around in this head of mine, but until I graduate to the next stage, I think these it’s safe to stop here.  There’s a whole new world of experience out there waiting for me to have.  I’m far more naive than I like to admit. I’d like to understand the answers from both sides, so tell me what you think and give it to me straight!


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