Dear SSG

And sometimes unsolicited!

On a new segment I like to call “DEAR SSG” (that is Sad Single Gal if you haven’t caught on), I will answer YOUR questions!

Dear SSG,

I have been hanging out with this guy, and he asked me out for dinner on a Thursday night. We are going to have dinner at a nice restaurant, so my friend told me I should wear a dress. I don’t really wear dresses, except in the summer. What do you think?


What To Wear

Dear What To Wear,

For your date, it is best to be comfortable. Wear clothes that you know you look good in, but also that you most importantly feel yourself in. If a dress isn’t something that you normally wear, why would you want to project that image, especially if you are just getting to know a guy (and since you are calling it hanging out, that is what I’ll assume the situation is)? So, remember to be yourself! Well, maybe not totally yourself yet!


Dear SSG,

The guy I am seeing invited me over to his place tonight for dinner, but said not to bring anything. Should I really not bring anything?

Empty Handed

Dear Empty Handed,

Get yourself to a wine store, stat! Didn’t your mother (or Emily Post? or Martha Stewart) teach you to never show up empty handed? Even if he already has a a bottle of wine open when you get there, I assume it won’t got to waste…



And that’s it for this first installment of Dear SSG! Wow! That was fun, right? Don’t you want to write to SSG and have her (me) answer YOUR burning (if it is really burning, go to the doctor!) questions? Well, write to or tweet me @sadsinglegal.

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