I'll start with a few general lessons I've learned so far. My dating experience has been almost entirely limited to girls I've met online (match.com and plenty of fish). When I first went online I thought "WOW, look at how many attractive girls there are, surely I'll have a date lined up every night of the week!" Over the next months I grew increasingly frustrated at how little action I got, in terms of responses from girls that I wrote emails to or "winked at" (match.com). It soon became apparent that it was precisely BECAUSE there are so many available boys online that these girls had become spoiled; rather than put any effort into dating one or more boys, most girls were seemingly waiting for "The One" to magically appear, say all the right things, and sweep them off their feet.
So over time, I arrived at my first rule, Rule #1: Maintain persistence at ALL times. Whatever your personal style is, stay with it and keep at it. Don't get discouraged, don't take time off of whichever site(s) you use, don't get bitter and don't ever, ever ignore potential dates that contact you. I can't stress this one enough…as much as we all want to think that we can idly wait around for that special someone to contact US, it doesn't appear to work that way. Take it upon yourself to be the one to make things happen, just like anything else in life the more you invest, the more return you'll receive.
I also soon arrived at one of my personal rules, Rule #2: Don't ever send winks, send short notes soliciting a response (so as to not inundate someone with too much reading or requiring too lengthy of a response; remember the KISS rule) and try to include something in the note that refers to the person's profile--brownie points are typically awarded to those who read profiles.
Rule #3: Don't be afraid to send someone a second note if they haven't replied to your first (or last) note. Remember Rule #1 (persistence), the receiver of your first note may not have been feeling up to the stress and pressure associated with this whole online dating thing. Try again and you'll increase your rate of success!
Rule #4: Keep things moving forward, all the time. Don't be afraid to mention meeting up sometime soon after making initial contact. While I never mention meeting up in the first note, I am not afraid to mention it after I've gotten 2 responses from someone (something like "hey, you seem pretty cool and down to earth, wanna meet up sometime?"). You don't want to get mired in an endless stream of back and forth emails or text messages. Often I will ask a girl out without getting her phone number first.
Keep in mind there are a lot of girls out there who are new to this and have never so much as met someone (from online) in person, so don't be discouraged if they don't appear to be that interested in meeting. Act like it's not a big deal, suggest meeting for coffee, and suggest that--much like a job interview--it's always great practice to meet someone on a blind date.
Rule #5: Be yourself. While I generally think most girls want someone to charm their pants off (no pun intended) on the first date, I acknowledge that this is not my nature. Therefore while I may sense that my conversation may not lead to a good night kiss (or more) with a girl, I do feel much more relaxed and at ease, and in turn this will help your date feel more comfortable.
Rule #6: This one cannot be emphasized enough--never insult or otherwise disrespect someone. All of us guys are truly in this together. More than likely you've seen one of the many negative profiles a lot of girls post indicating they've been mistreated in the past. The guys that do this are making it harder for the rest of us. If you make contact with someone and it doesn't work out, ALWAYS thank them for their time and wish them luck, no matter how frustrated or discouraged you may be. You WILL be a better person as a result, and this will attract others to you!
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