Nah, your friend is an ass – you shouldn’t be making out with her on the first … (I was going to say “outing” instead of “date,” but maybe that’s not the best choice of words, either. ) When the time is right to move to the next level, you’ll know. (You might want to break the ice by giving her a peck on the cheek after your next date if you had a good time and enjoy her company.)
Glad to hear it went well. Keep us apprised! We’re rooting for you!
Give her a kiss on the cheek when you drop her off after your date. You don’t need to pressure yourself into doing anything more than that!
I think your situation is really great. I know everyone else has said it, but just be yourself. Don’t worry about what you’re going to say and when to say it. Sounds like she’s interested in you, and why would you try not to be yourself?
Elysian’s got a sound plan… But of a kiss seems too forward, you can always try a nice hug at the end of the evening. Smile real big and say with your arms outstretched, “Can I a hug?” If she likes you (and it sounds like she does) there’s no way you’ll get turned down. It’s not too threatening, and if the hug works out really well it’s a perfect segue into the kiss on the cheek. Plant a quick one, smile your warmest friendliest smile and say “goodnight.” That’s all there is to it.
Or, you could hug her – or peck her on the cheek – when you feel comfortable, and not worry about how many dates it’s been.
Also, a great way to really get to know each other is for each of you to bring a friend or two out to dinner (a table of five makes for great big conversations because it stops people from pairing off). You not only get to hang out with each other, but you get to hang out with each other’s friends, meet cool new people, and no worries about awkward silences. If you two happen to show up in the same car, or go home in the same car, so much the better.
Remember, she’s a person, not a misterious alien! You’re a person too.
Courage is facing and overcoming your fear. You are showing courage in doing this. And over time, your fear will go away. You’ve already done the hard part, now it just gets better.
-Former very shy guy, now happily married, sleep deprived new Dad.