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Timing is Everything

September 19, 2018

 

 

I had a really great first date which ended with the intention of a second date.  Never heard a word back from him, which of course bugged me but I got over it.  Three months later, he leaves me a message and wants to get together.  What should I do?

 

Sometime life gets in the way, and maybe there’s a good reason for your date’s tardiness in responding.  If you hear him out, you’ll know the reason and you can decide if he’s worthy of another shot.  He might just make your second date worth the wait.

 

I matched with a hot guy on Tinder.  After talking with him, I realized that I dated him a few times twenty years ago.  We’re getting together… should I tell him?

 

That’s actually pretty cool and you should point it out to him, but not straight out of the gate.  Go on a date and have some fun in the now before taking a walk down dating memory lane.  Timing is everything and maybe the right timing is now, but the only way to know is to focus on the 2018 version.

 

I saw my friend’s Ex in a bar, and after a conversation and a couple drinks we hooked up.  They are not on good terms and my friend’s cheating caused the breakup.  The problem is that I like him, the sex was great and he wants to date.  Should I?

 

If you really like this guy and you really want to pursue him, you should.  One man’s blunder can be another man’s buffet, so grab a plate and start enjoying.  As for your friend, the classy thing to do is let him hear it from you.  Give yourself at least a month of dating, and if your new romance appears to be going somewhere you need to tell him.  When you do it, remember to be kind, honest, and ready for any reaction. 

 

 

What 300WORDS are best for you?

Email your question and the next 300WORDS might just be yours!

 

crogersnyc@gmail.com

 

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@CraigRogersNYC

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