So I've been having most of my success meeting women online via tinder. However this date of mine last Friday did not go as well as I had hoped.

This girl, Aly and I go out for dinner in Regina. Originally my plan was to have a quick bite to eat before going for a walk together in the park. Unfortunately, the restaurant I had in mind near the park was full, and it was absolutely freezing outside. I improvise by finding a nearby place to eat instead. The whole time we're talking about her history in music and how she's spent most of her life travelling across North America. There's never really an awkward silence between us throughout dinner, but I think I dropped the ball when I suggested that, in the spirit of Valentines Day, we share some wine I had brought back at her place. (I live out of town.)

She declines, insisting she never brings guys home on the first date and that it was enough of a stretch trusting me with her address. I drop the topic and we continue on talking about family, friends and the drug problems in Regina.

As you can see, the main issue here is we lacked any physical escalation. I was able to wrap my arm around her after dinner and hold her hand in my car, but instead of playing pool like I suggested, she insists on calling it a night because her friend needed some consolation (BF dumped her.)

I had bought the wine because I read a guide somewhere on here about using the offer of drinks as a method of escalation. It seems like this only works if you can build enough rapport early on in the night. Unfortunately, we weren't able to really "click" (hardly made her laugh aside from a story of mine in Mexico) and all I got was a hug goodnight. (I Hate waiting until the end of the night to kiss.)

The next day I text her saying how I had fun. She thanked me for a great night. I tried continuing the text conversation by asking about this Celtic tattoo she planned on getting and whether or not she was nervous. Alas, she reads my text and gives no response. Should I even bother trying to call this girl to set up another date? I have since made a new Tinder date with another girl for this Friday.

There's a few questions I have to perform better on my next date this Friday (with the new girl):

  1. Should I even bother bringing up the wine unless I can manage to kiss her first? (We're going skating instead of eating out, so that'll at least offer some physical contact.)

  2. How do I avoid being BORING? I felt like this was my greatest mistake last Friday, despite having plenty of hobbies to talk about, I never really made the connection I was looking for.

  3. Are there any decent ice breakers I can use for next time that will start building actual connections as lovers instead of us just feeling like friends?

  4. MOST IMPORTANT: how often should I text this new girl between now and Friday? Should I try calling her later this week to confirm our date (say Wednesday), or stick to text messaging? I noticed that a few hours after securing her number and chatting a bit via text, my tinder conversation with this new girl has disappeared! Should I be concerned at all?