Look, I know I’m not exactly “Mr. Perfect” when it comes to dating, and I’m sure that during the course of a date I’ll say or imply something that might not be exactly right for the occasion, but I assure you it all comes from a good place. Additionally, I will freely admit that I am not someone who is particularly good at reading signals during a date, which has led me to interrupt much of how the night went based largely on how things end. However, in saying all of that, regardless of how I think a date went, at the end, no matter what, I am going to offer two things; 1) That I pay our bill and 2) That if she didn’t drive I either walk her home or give her a ride.

Call me old-fashioned but since most of my dates are at night I’m just not going to part ways with a woman until I know that she can get home safely. Since I always arrive at dates straight from work, and therefore have my car, there is no reason why I can’t extend the evening a few minutes in order to give my date a ride home. However, even though I originally began offering rides to my dates because it seemed like the gentlemanly thing to do it has caused an unexpected problem to arise.

You see, whenever I have what I consider to be a good date, and afterward I give her a ride home, the moment that I drop her off is always very awkward. The problem is that when you are sitting in a car there is really no good way for her to say goodnight that would give me an overt sign as to whether or not she wants to go out again. If we parted ways outside of the restaurant, or after walking her to her car, then I might be able to get a better feel for how she thought the evening went based on how we say goodbye.

Unfortunately, when I give a woman a ride home there is really no opportunity for any type of physical goodbye, such as a hug, which makes the moment the date ends an awkward one where we are both caught in goodnight limbo. Sure, she can still say that she had a nice time, but I’ve heard that from too many woman who have ended up declining my request for another date. Therefore, that goodbye is no longer enough to fill me with confidence. Ultimately the onerous is on me to pay more attention to the signs she gives me as to how things are going between us during the date since I know that if I give her a ride home, I may not get a good opportunity to judge things at the end.