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Alexander,
A girl that I met online and have been out with twice has invited me out with a friend of hers and her boyfriend who supposedly is in from out of town. Our two dates have been fun but casual, and by no means are we acting like anything resembling a couple at this point. I also have not made up my mind yet where I would like to take things with her (I am 10 years older than her). Should I go?
Stan
Miami
********MY RESPONSE********
NO.
Even if you knew what your plans were for this young vixen, group dates are a BAD idea this early on (especially HER group).
My general rule is that for the first sixty days you are interacting with a women, it is just the two of you out on dates. No friends, cousins, pets or mob-connected uncles.
I see very little good that can come out of going out under this type of arrangement. Let's look at why:
First, you are going to be tested and judged. BIG TIME.
You and her friend might be old chums by the time she is the maid of honor at your wedding, but I can assure you she is NOT on your side tonight.
If you have done everything right up until this point, your date should be pretty into you by now. When a women likes the guy she is out with, certain mistakes men inevitably (and unconsciously) make tend to be overlooked.
However, her friend's role that evening will be to make sure your lovestricken date is not letting too much slide. Shoes don't match your belt? Busted. Undertipped at the restaurant (or overtipped and acted like a douche bragging about it)? Busted. Checking out your date's ass at the bowling alley? Busted. An extra pair of eyes on you this early is never good.
And then you have to prepare for all of those questions her friend is going to throw at you. It's a safe bet that they are going to be of the 'job interview' type - you know, the ones we all go through great lengths to avoid in the first place (perhaps this is her way of finally getting those answers you wont give her - clever, eh?).
Finally, she is NOT going to be acting the same way she does when you are alone. Think she is going to chuckle again when you try that 'stop-short' move in your car in front of a girl she has known since she was 6? Think again. And you can forget about trying to make a move on her in front of her friends. Then again, why would you want to?
Decline her offer (politely, of course) and counteroffer with another day where it can just be the two of you. Once you guys are a happy couple that has been together for at least two months, then you can meet her friends (and vice versa). Until then, no group dates!
Alexander Stone & Stephen David
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Online Dating Edge / Approach Dynamics