Passenger Seat or Driver??

I met Jeremy several months ago at a mutual friend’s cocktail party and we immediately hit it off… he was intelligent, witty and perfectly sarcastic. After an evening of chatting over cocktails and appetizers, we exchanged business cards and emailed for a few weeks before he suggested we “hang out sometime”. At that point, I suggested some dates and times that I was available, none of which seemed to fit with his schedule. A few weeks later he sent another email, inquiring about my schedule. This time, I simply provided my phone number and suggested he call to discuss. He called a week later. After an hour-long conversation, I was reminded why I had kept in touch with this guy for so many weeks – conversation easily flowed, we laughed a lot and he really seemed to listen and thoughtfully respond to my comments. After a few awkward questions about whether I would like to actually hang out in person (ummm, yeah…duh!), we finally settled on a date to “hang out”.

The date itself was terrific - a day visit to a much-anticipated museum exhibit as well as afternoon cocktails, followed by a lovely dinner. The entire event was extremely well planned. In fact, I even caught a glimpse of a computer-printed sheet of paper listing the names and addresses of all locations we would be visiting, starting with my home address and time of pick-up (Jeremy immediately got points for being very well organized!). He also brought bottled water and sunscreen as much of the day included outdoor gardens. Being together was comfortable, easy and fun. He even referenced future activities that we might enjoy together as well. The date ended with Jeremy very gentlemanly walking me to my door, inquiring whether I really, “honestly” had a good time, a quick hug and an immediate departure back to his car.

It has now been five weeks since our first date. At his initiation, several emails have been exchanged, each commenting on how much fun we had on our date. He even texted me one evening to inquire what I was “up to”… I responded that I was out with our mutual friend and he replied that he was visiting his family several hours away...okay… Our most recent email exchange was an email from him “touching base” and once again, suggesting we “should hang out again soon”...


Lemons: While I truly appreciate Jeremy’s thoughtful planning and respectful approach to our date, I cannot ignore his obvious hesitation. To use a car analogy, I don’t mind driving but definitely hope to swap seats every now and then. I tend to think that being tentative in something like simply initiating a second date may also indicate a tendency to be tentative in even more important topics in the future such as asserting one’s opinion, feelings or initiating discussions on difficult topics. Agree or disagree??