Hi Meredith,

I’ve always been the single friend. The fun friend you can count on for a Saturday night out or the one you know doesn’t need a date to your wedding. It’s been OK because I’m very independent. I travel a lot for work and I have a lot of different circles of friends to keep me busy.

I’ve tried online dating on and off. Recently I’ve decided to take dating a bit more seriously. In the past two months, I’ve been on five first dates and two second dates.

Certain dates have had more chemistry than others but for the most part, all the dates go on for hours longer than planned and end well with passionate kisses and his promise to call. Then he doesn’t.

After four days or so, I’ll send a friendly text which leads to short banter but no invitation for another date. I know I can ask him out, but I’m a bit old fashioned and a believer of “if he wanted to, he would.”

It makes me so confused. I then over analyze the date looking for clues as to what I did wrong. If the date had ended poorly or even with a handshake, then I would understand, but all the signs were there that he had a great time. I’m starting to get really discouraged by dating because I am constantly doubting myself.

Was it something I said? If it wasn’t something I said, then is it how I looked? If it’s how I looked, then why did he kiss me? Dating is actually destroying my self-esteem. Should I just start investing in cats now?

– Plenty Of Doubts