Flirting on a Dating Website

When you’d like to try flirting on a dating website, you have literally hundreds of possible choices, several of which have over one million members, all of whom are trying to meet somebody.  It’s as if everyone started wearing t-shirts that said “approach me” or “leave me alone”, along with their sexual orientations and lists of their interests.  Before you begin testing out your skills on the online object of your affection, it’s important to remember that although people are looking for different things—from friendship to one-night stands to marriage—almost all of them are looking to eventually meet offline, so if you’re only looking to flirt online, chat rooms might be a better bet.  Otherwise, many people will get bored or feel cheated when they realize that you never intend to meet face-to-face.

A good way to start a conversation with someone on a dating site is to send her a message (most dating sites have a mail function) asking a question about something you read in her profile.  Don’t ask something that can be answered with a “yes” or a “no” or that’s likely all you’ll get.  If your question and your profile are interesting to her, she’ll likely respond with some information about herself and a question or two for you.  If the first response is lacklustre, but doesn’t seem dismissive, it’s probably okay to send one more.  She might have been busy (women tend to receive a lot more mail than men) or having a bad day.  But, if the second response doesn’t come or is awkward or boring, ditch the conversation and try again with someone else.  It’s not worth wasting your time on correspondence if you’re not having fun. 

If you got a positive reply, hold your horses.  Don’t fire off a response right away.  Wait between one and 24 hours before replying.  Switch up the time between replies as the correspondence continues.  Don’t be predictable.  You don’t want to seem over eager, and people who have busy and interesting lives don’t usually have a lot of spare time to spend online.  Generally, keep your e-mail and chat messages three to five sentences long.  This is long enough to stand out from the endless numbers of “heys” and “ur cutes” that clutter up users’ inboxes, yet short enough that she’ll read it when she receives it, not tell herself she’ll have time later then forget about it. 

Did I say “chat”?  Several dating websites have a built-in chat function.  Others may not, but you can always invite someone to chat with you on Yahoo, MSN, or Skype instead.  It’s best to start out with mail because it isn’t in real time and people can respond to it at their leisure, making them feel less pressured.  You can ask if the other person is interested in chatting after you’ve exchanged a few messages.  If she doesn’t take you up on it, don’t take it personally.  Some people just prefer e-mail, especially if they’re doing their flirting from work!

Whether you’re flirting with someone online or in person, it’s important not to overdo it.  It can make you come across as creepy and desperate.  Be yourself and relax!  When you are teasing someone (one of the most important parts of flirting!) or saying something that could be misinterpreted, you should employ emoticons, such as :-),  :-p, and  ;-).  Typing words divorces them from your intent since the person can’t hear the tone of your voice, see your facial expression, or read your body language.  Remember, with emoticons, less is more.  If you use too many, you’ll come across like a teenage girl (which isn’t likely to appeal to the demographic you’re interested in).   Always keep your conversations positive.  Save your problems for your offline friends.  You want to ensure that the other person is enjoying your conversation and wants to talk to you again, so don’t be a downer!  To ensure that the person you’re corresponding with always hopes to see you online, say something interesting before you go.  Don’t reveal too much detail, just give her enough to make her want to know more next time you’re online.