Dating at 40...Mis-Matched Expectations?

Recently after talking to a girlfriend of mine, I began to ponder the challenges in today's dating scene. Is it harder for 40 somethings to re-enter singlehood and date again?

As we talked I was amazed by the challenges she faced as a single woman. In particular, I began to wonder, "Are 40 something men looking for the same things in a relationship as 40 something women? Or... are budding relationships being strangled by mis-matched expectations?"

My girlfriend, who I'll call Chloe is a professional, divorced mother of two teenage boys. She has a very eclectic and artsy personality. She is well read, a dedicated runner, and cute. She never has difficulties meeting men, however, meeting the "right" man seems to be the problem.

Recently she was dating David, who seemed to have great potential. He was a great conversationalist, well read, extremely handsome and had a great job. One night, he invited her over to his apartment where Chloe discovered he had no furniture - nothing but a bed and television. "What 40 something man has no furniture, she asked?" After giving him the benefit of the doubt she was pleasantly surprised to be invited on a weekend getaway with a group of David's friends. That is until he explained that due to his lack of funds they would be carpooling with another couple AND rooming with a group of his friends that she had never met. Unless, of course, she wanted to pay for the hotel stay. "His funds were low."

Finally after several more conversations with David, Chloe decided that it was time to terminate the relationship and move on. While David had a successful career, he was an irresponsible spendthrift with bad credit looking for someone to help him get established. At 40 something? Typical or bizarre?

Before David, there was Keith. Keith was another professional 40 something that Chloe had agreed to go out with on a blind date. Prior to going to dinner, the two enjoyed numerous engaging phone conversations. Chloe eagerly anticipated their first date.

They met at and Italian restaurant. Chloe immediately extended her hand in greeting. Keith reached for a hug. Chloe explained that she was not comfortable hugging immediately and Keith seemed a little offended. Throughout dinner, Keith attempted several times to either hug or kiss Chloe who was becoming increasingly uncomfortable - after all it was their first date. Keith on the other hand was becoming increasingly agitated. The date goes downhill from here.

Keith began making rude comments and Chloe became defensive. By the end of the night, in Chloe's mind, Keith was a controlling maniac and escape was imperative. After paying her portion of the check AND giving Keith a piece of her mind Chloe fled the restaurant and Keith began chasing her! How did a potentially great date go so incredibly wrong?

Are men and woman really looking for something so distinctly different at 40? I always believed that most men and woman after exiting their 20's are looking for stability. You know...loving relationships, starting families, settling down. Is this an erroneous assumption?

While Chloe is not looking to get married tomorrow, there is the hope that eventually she will marry again. Now in her 40's the thought of entering into a relationship with a man who is financially unable to care for himself is undesirable. In addition, being in a relationship with someone who becomes critical when unable to have his way or assert his authority is a bit frightening.

Is this typical of 40 something dating?