Lisa is a safe choice. She represents something he wanted during his last days before hell. Especially after he met Ben. He realized he wanted a family, leave something of himself behind. She came ready made without him having any deep emotions other than liking her. How they met, actually sets the tone for the relationship- "no risk" just a bloody good time with a beautiful girl" ( Ben cannot be Dean's son because it takes 10 months to incubate a fetus, and Ben is a year older than the period between his first and second meeting with Lisa. If Ben is his he will be a year younger).
See, he can't even dare hope of ever having a family with the ONE. Bad acting or personal dislikes aside, Cassie got him good.**Did you see the smoking hot scene in route 666?**. He fell for her , so deep that he fessed up to a civilian about the family business. Dean is a good soldier, he does not disobey John, but this one time he did, hoping that it will last. Dean dared to love, to hope and to wish for a future for the first time . He risked an important part of himself to try to be with her. He was also with her a lot longer than 2 weeks. The "couple of weeks" explanation had been a glib response to get Sammy off his back, but he did later admit they were a lot more involved than the picture he painted earlier for Sammy. She touched him like no other woman will be allowed to ever again. He is still in love with her. However there are numerous reasons why he doesn't go back. As he got more and more involved in some unbelievable escapades, he kept pushing his needs aside to see to Dad and Sammy. Then all of a sudden, its 4 yrs and he may reason that she moved on. Given thier prior history and his promise to return, he might think she will REJECT him after 4 years of absence. He could also have reasoned that she had a shot at normal without him and could have been scared that Cassie will end up like Jess and Mom-Mary.
The first time around , Cassie loved Dean , she never stopped. Being in love and building a life together are two completely different things that may not always be compatible. She was running scared because falling in love and your emotions being dependent on another is SCARY. Scared people do crazy things. An independent person like Cassie with her future all mapped out will more scared than most. She will latch onto an excuse to run, very far from the one thing that confuses her and endangers her well planned future: Dean, the person who has the power to turn her world upside down.
Can you blame or hate Cassie for her reaction- imagine falling for someone really hard, who keeps disappearing, returning with injuries without explanations . Then imagine you are not a "believer" but head over heels in love with this guy who fesses up and says " I hunt ghost". Dean is a player, and if a player tells you this, your first reaction will be that he wants to dump you and move on. Even if he wasn't a player, 99.9% of sane normal girls will go beserk if told what Deans does for a living. Dean has always been aware that telling his job makes him sound crazy! Cassie needed to experience Dean's life first hand to believe and accept him fully. This is how Lisa gets to know about the family business-she and her son were in danger. It required no explanations from Dean and again no risk what so ever. Lisa really makes life easy. No work on Deans part with this chick.
Cuddling after that hot hawt hot scene -"sorting things out" –according to Sammy :)) I can extrapolate that Cassie had already experienced the side effects of the family business on their prior relationship. Because when she says "if you try hard enough , you can make anything work" he responds: "but I am still REALLY involved with my DADs job". So I imagine the scenario was that , he told some glib stories about the family business to explain his absences and injuries in Ohio . As a journalist, she probably pushed for details. He finally tells her when they are about head out a lot further than Ohio for a longer period, so she doesn't think he just walked out on her. Then like any normal girl would, she flips out. He is lucky she doesn't call 911 or have him committed :). Dean usually gets involved with women who never seek or need explanations. Lisa does not want any either. Cassie is smart and he knows she was not just someone you could string along with glib explanations forever especially when you want forever.
*** Little miss perfect , college educated queen of small town Cape Giradeau falls, and I mean falls like a ton of bricks (they were even conidering a future together ) for some psycho dude with no interest in college or NORMAL ambition , who claims to hunt ghosts, also has some serious arsenal in his trunk. Scary and heartbreaking for her to lose out on love like that, thinking she has been duped by a crazy man*** I bet the first call was to daddy and Mom to pick up the pieces :)- She is an only child afterall (hmm maybe a later episode where Mrs Robinson puts 2 and 2 together on Dean and Cassie) -**
Second time around (Route 666). She is now a believer of sorts (at least in ghost trucks :)). But she can't ask him to stay. Some can love enough to let go when they need to. She does not want to hold him to promises that may not get fulfilled. Besides heroes are for the world to share , not just one person. Wow, what a love rectangle : Dean , Sammy Cassie and the world at large :). Cassie is a realist but love hopes, and by saying that to Dean, she was giving him an out." No expectations, no clinging, just go and save the world but maybe , just maybe if you come back one day, I will still be waiting." What kind of relationship could they have had with his hunting and taking care of Sammy; and how resentful would she have gotten with his absences. Love may be there, but you have to know your limitations. And sometimes one has to love enough to free the lover. Can't blame Cassie for wanting normal, even Sammy wanted a normal life.
I understand why he returned to Lisa, she was the most recent emotional attachment and represents his idea of a ready made apple pie life. Albeit the weak emotional connection. However, By returning to his weekend fling, Dean was fulfulling his need to have a family without putting himself out there emotionally for Lisa. Lisa has a son and Dean actually relates to kids pretty well. He wants what they have and family is the most important thing to the Winchesters. He will and can make a good husband if he puts his mind to it, but there will always be something missing, because his heart is already taken. Its like living in black and white when you can switch to technicolor with Cassie. Its called "settling" and a lot of people do it all the time, when being with the ONE is just not feasible.
The Season 5 finale would have been more satisfying had he made it to go see Cassie. Maybe to find out she built a life for herself as a respectable journalist , writing about the supernatural on the side and raising their child. A child is a constant reminder of the father, and can make Cassie hold out for Dean after all these years. This time around she will be more willing to consider a life with him. Because now, she will know that even the best laid future plans do not necessarily make you ecstatic. Cassie will also be living in black and white, when she can live in technicolor with Dean.
** What can I say but that I am a romantic who believes in the power of first and true love**
I just watched the entire show this year when the show moved to TNT, else I would have never known it existed. Jensen Ackles is a really good actor, who will translate to the big screen really well.
I do not think Megalyn is a bad actress. I have seen her work on the 4400, Law and Order as a journalist , CSI Maimi as the coroner and the law show with the guy from Angel. I think she does a superb job of taking on the roles of professional independent women. Her work in supernatural though was a bit lacking. I presume she was supposed to act nervous and skittish around Dean. BUT that sex scene was HOT. She nailed that scene real wellJ. She has enough acting chops do the role of Cassie justice if she is brought back.
She had mentioned somewhere that she was excited about CSI Miami because she didn't have to play someone's GF or daughter etc. I doubt she enjoys playing the role of the token girlfriend though and her role will be limited because supernatural IS really about Dean and Sammy. But the role may appeal to her, if she is cast as a successful career woman-journalist . She has a habit of showing up on super successful shows in the final year or so.
I think most people hate Cassie primarily because the CW audience may have missed the nuances- the depths and layers of the exchange between Dean and Cassie . Plus the Fan girls/boys prefer a single Dean and Sam. Cassie threatens the image of a forever unattached Dean and their fantasies in regards to Ackles. J . To make Cassie work on the show, she has to earn forgiveness from Dean and his fan girls/boys.