Y'know, it's kind of interesting that a lot of people pair Tara with Darren. In my game they showed up in a welcome wagon together and almost immediately started sucking face. I forgot to check their turn-ons, but I did find out they had triple bolts! A quick glance at the Sims Wikia shows that they have very similar personalities and one of the stronger aspiration matches, so that's a good starting point. The rest is luck (barring the player changing it, of course), thanks to random turn-ons and turn-offs.

Edit: oh nooo the top post isn't even about Cassie. I already said all my feelings about Cassandra x Don and Cassandra x Darren earlier, though. I think I might start a separate save and play the Goth house just to see who she's most compatible with in this save. Again, I have no idea what her turn-ons are, so this should be fun; I remember a much earlier run rolled the wrong turn-offs and actually gave Cassandra and Darren very low, possibly negative chemistry.

Team neither. I usually have Don marry Kaylyn Langerak, and make sure that Don and Kaylyn's work schedules allow him to occasionally carry on his antics, but establish a family to fulfill Kaylyn's dreams (Kaylyn has a family aspiration like Cassandra). I've done different things with Cassandra, usually it's involved giving her a make over and having her hook up with someone I made specifically for her, although now that I have OFB, I'm thinking about having her marry Malcomb Landgraab. Either that, or I'll have Nicole Smyth (part of the Smyth family, my family of military Sims whom trace their roots back to The Sims 1 as my first successful family) have a brother this time and hook Cassandra up with him; I think the conservative Goth family with the conservative Smyth family would be a good match, especially seeing how the two families were friends in TS1.

I decided to start a new Pleasantview, and in it, Cassandra rolled attraction to blonde hair and makeup. I'm setting her up with Dina Caliente. I plan to make Don a plantsim and Nina Caliente will run a sexual therapy business with him. And Darren will... I dunno. Bore me.

To be honest I think that almost everyone in Pleasentview (well, not regular townies) are idiots, i just like the Broke family and Bella Goth.

Unfortunately after the Pleasant daughters went off to college both Daniel Pleasant and Don had a terrible swimming pool accident. To get over this awful tragedy Cassandra and Mary Sue had a makeover and bought a vacation home in Twikkii Island where they seemed to move on pretty fast. Darren sometimes joins them as well.

This last time I played Pleasantville, Cassandra had relationships with both men, although not at the same time. Since she was so keen on Don, I let her marry him and then get her heart broken when she found him fooling around with the maid. She threw him out of the house and called her old friend Darren. But she still felt bad about Don and started talking to him. One afternoon, things went too far with Don and Cassandra decided it was time to move on. She let Don go and forged a new relationship with Darren. It wasn't long before she realized she was carrying Don's child. Make that children. She had twin boys who, although they are in their teens, have yet to meet Don and believe that Darren is their father.

Team neither. I don't play Pleasantview except for playing the Goth house for a few days when I first got the game and extracting Mary-Sue and the twins and having them in another hood. I never quite got the popularity of the place. The only pre-made hood I played often was Strangetown. Interesting genetics.

I had her marry Don out of her love for him, but then he inevitably cheated on her and they broke up. He drew three bolts for a woman who looked exactly like Bella Goth though in the game, so he's committed to her now. (I play with clean templates, so the real Bella is married to Jason Larson). Darren is too good for Casandra, in my opinion. He found a townie woman to marry. Mortimer stepped in and arranged Cassandra's marriage to Armand DeBateau.

I actually paired Don up with Dina, and had Nina marry one of my custom-made sims. This left Darren, so I actually got him to marry Cassandra and start a family with her.

I got Cassandra to marry Don but he had Ugly kids and Nina walked by so..... yeah. Cassandra left Don. i'm going to get her married to Darren and hopefully have beautiful kiddies. but yeah, Don wasn't right for Cassandra, plus he hated his two children. (Kennie and Scarlette.)

That's so sad, about Don hating his children. When you first said, "Nina walked by so...yeah". I thought Cassandra was leaving Don for Nina. Now THAT's a twist that would be interesting. I could just see Don's reaction.

In my hood, after Cassandra threw Don to the curb and after a few empty affairs, Don fell under the spell of the hapless and fertile Brandi Broke. He's curbed his wolf-like ways and Brandi is studying up on how to handle anger.

Dreamer and Lothario on the side!
This is totally by Cass's choice. In the beginning of this version of Pleasantview, Cass was at Darren's house being won over and wooed by Darren when Don came by. Don was jealous and basically broke off the engagement! She and Darren are happily married, but he is an elder and wants to paint all day.They have a cute little baby, but Cass has a problem. She doesn't get the 'attention' she needs from her husband. Once she did Woo Hoo for the first time, she found she wants more!! That's where Don comes in. He is currently trying to Woo Hoo 20 Sims and is up to 11, but has to juggle it all. It's not a pretty sight! He won Cass back and satisfied her Woo Hoo need (if you catch my drift)! She keeps rolling the want to "invite Don over" and 'flirt w/ Don", etc. So, they have an on-again-off- again relationship.
Someone has mentioned Tara Kat in a previous post. My Tara is pretty much the town whore and is currently pregnant w/ Don's baby. When she moved into her current home he called for an outing. The outing consisted of Don and 6 of his f...-buddies! One of which was Cass.It was pretty funny. Of course someone made a move on Don and all of a sudden he has the rest of his women all smacking him and being pissed off! Right now I am working on damage control, but who knows...they may get together yet! My goal for Don is to end up with whoever he is the highest with after 20 Woo-Hoo's! Perhaps Darren will have croaked by then. He is pretty old.

Team Dreamer, because she should get a good guy (and I loathe the "redeemed by the love of a good woman" trope). Kalynn, OTOH, is foolish or selfish enough to get involved with two men she knew were cheaters, so I had her move in with Don, then trick him into getting her pregnant so she can have the baby she's always wanted (and she was desperate because I timed conception for her last day of fertility).

I like to go for Darren - he's such a nice guy and would give Cassandra the attention and love she needs. Might try and have her marry one of the Curious brothers instead though - that sounds quite novel! Gotta fix the house though, 'cause the way it's designed the routing is horrible!

I was team Dreamer for a while, but I tried being Team Lothario! At least. In the end, I'm team Gieke.

In my Uberhood though, Cassandra might run to Veronaville, where she'll fall in love with that Monty guy who has two kids.. Antonio, Beatrice, and Benedict. I think they'll make a good couple. So team Antonio in that case.

I also had Darren and Dina get together. My philosophy was this. Darren had absolutely no $ so Dina couldn't be accused of going after him for any reason other than love. Never thought about the widow thing, good point! Dina had a great drive to be successful so she blazed her way through the medicine career track and Darren was able to do what he loved, open an art gallery at the back of their home. And Dina got there on her own merits. They became extremely wealthy and have a home high on the hill. Their ancestors live there and couldn't be happier. Dina and Darren were really great together and very loving. They are buried with platinum graves out by a pond on their property. Darren's son Dirk and his wife Lilith (I did keep those two together) are now elders and their son Linus and his wife and their kids live there as well. I'm very happy with my pairing.

In other news, Nina went after Mr. Big. Which is too funny in my book since Dina is supposed to be the gold digger.

My choice is team neither, too.

Cassandra and Don end the engagement amicably and part friends. She wasn't all that into him after all since they shared almost nothing in common, and although he would have gone through with it, his feelings were pretty much the same as hers at this point. Cassandra stays in the Goth house until Mortimer marries Dina and then moves out, again without any hard feelings. If Dina can make her father happy, Cass is happy, too. She is living in a rehabbed brownstone in southwest Pleasantview near the bay, a culturally diverse area known for its restaurants and galleries. She's enjoying her career at a robotics firm specializing in nanotechnology and is not in any hurry to get seriously involved again.

Don is absorbed in his job and casually dating. He fired Kaylynn since he wasn't comfortable about the thing with Daniel Pleasant. He didn't care about Kaylynn's personal relationships (he's not a hypocrite), but sharing with Daniel creeped him out. His relationship with Dina never went beyond a mild flirtation, and that ended with her marriage. The sisters are close. It wouldn't have worked, and he didn't really consider it an option (not that he didn't fantasize). He spends most of his free time with Nina and would like it if she moved in with him. That's 'move in', not marry. Nina is hesitating; she believes living together will cause problems and potentially destroy their friendship. She may change her mind. She's tired of living in that house she shared with her sister, and if she goes to the trouble of moving, she may as well move in with the man she's so close to.

Darren fell madly in love with Brandi Broke whom he met at a block party thrown by Tara Kat. Cassandra was more his muse than a woman he was actually in love with, and she certainly wasn't in love with him. Brandi had her baby before they married. Between the two of them, they already have four children. It's unlikely they will have more. They moved to the same area where Cassandra lives, in a brick loft with room for an artist's studio. Darren met a local art gallery owner and has had several shows. He is doing quite well.

Ha ha. Why? Very curious!

Probably because it doesn't work in real life, but women keep trying it. (As do men, but there's no "redeemed by the love of a good man" trope.) No one is redeemed by anybody else's actions, only their own. Redemption is work, and no one can do it but you.

Now, it does happen that, once you've hurt someone really hard and faced your responsibility for that, you're motivated by your love for that person to do the hard work and redeem yourself; but that's awful hard on the second person in that scenario and it's a mug's game to count on it.

Just as bad is the one where reality is - completely - thrown out the window with, "I thought I could change him/her."

It's all tied in with my strong dislike for the "bad boy" character on television. He sleeps around, cheats on people, uses people, treats them like crap, and yet we're supposed to root for the heroine to win his love? Why? He's an asshole. I don't want her to "redeem" the asshole - I want her to go for a guy who already knows what respect, honesty, etc. is. I always love the nice guy. I just don't get "bad boy" appeal. All I hear is "sure, he's shitty, but he's not really shitty, he's sunshine and roses and perfection, if only someone would believe in him....'cause he's really hot" Gag. Redemption must come from within, IMO. A person has to want to change first. They have to actually regret the horrible things they've done and not just stop doing them because doing them keeps them from getting what they want - then it's still a selfish choice. They don't change because they were wrong, or because they cared about the people they wronged - they change to get something/someone. And I can have no respect for a character who falls for selfish liar. I cannot fathom how you can love someone you know is like that - I just can't wrap my mind around it. I loathe bad boy characters. Redeemed by love is a classic bad boy trope, and I loathe it, too. I don't get/like characters who fall for selfish assholes. Falling for someone who used to be that way but has improved themselves as a peson is all well fine - falling for someone who still is that way is just wonky. And then he's suddenly good for no other reason than she loves him - nope, don't buy it.

Side note: I adored how, in the first season of Gilmore Girls, Rory was completely disinterested and turned off by Tristan and waned nothing to do with him (lots of fans disagreed with me). It was fabulous, a breath of fresh air. Absolutely wonderful. I quit watching very early in the second season for very obvious reasons.

Team Dreamer, the hopeless romantic deserves Cassandra more than the love rat!

Usually I go for Team Dreamer. Cassandra usually marries Don, has one child, divorces him, marries Darren, has one more child and they raise their big happy, modern family together

This time though I'm doing things differently. Cassandra still married Don, but their going to stick it out for a while and have 2-3 children. Cassandra will divorce him eventually when she finds out that Don has also fathered twins with the ex-maid Kaylynn, and is continuing his affairs with many other women.

I've got Darren together with Florence Delarosa. They live in her (expanded) house, Florence still running the business with some help from Darren and Dirk, while also raising their daughter. They actually make a really good couple. Their closer in age, have the same aspiration and keep autonomously flirting and being romantic all the time. Plus Dirk gets some business experience before setting out to expand an empire of his own :D

Team Antonio Monty!
I've done all sorts of things with Cassie: Malcolm Landgraab, Don Lothario . . . but with Antonio Monty, the first thing she did was roll the wants to be friends with her stepkids. And then continued rolling wants for them as if they were hers, together with the regular newly wed family sim wants. I think this next time she might end up with Armand DeBateau in the end. A lot depends on just how things go with Don--if they get married then divorce or not. Who appeals, and who's available, at the beginning of gameplay, and who appeals and is available a few years down the road . . .

I've played Pleasantview quite a few times in the past, and I've had Cassandra (one of my least favourite characters in any game/book/film/tvseries EVER) marry Darren, Don, John Burb, Malcolm Landgraab, Jason Larson, Dirk Dreamer, Chester Gieke... She's even lived alone, or as a cat lady. To me, she is desperate and broken, probably because of her mother's abandonment. With Darren, she is happy, but I don't feel that its "love" on her part, I feel its more of a "I really appreciate you loving me". And they are pretty good together but also boring. With Don, Maxis what were you thinking?! The only way to make this work is to rewire Don, and that just ruins his character. To me, Don needs to be single, have lots of affairs, a few kids here there and everywhere, and die the Playboy of Pleasantview. John Burb is too middle class to be believable - Mortimer would only accept, out of those listed, Malcolm and Darren I think. Malcolm because he can provide for Cassandra, what with the money and the reputation and I think someone earlier said "old money"? Or Darren, because although Cassandra may or may not truly love him back, he treats her gently and with respect and Mortimer would appreciate that. It's all a matter of opinion - if you think Cassandra would be more swayed by money, reputation and her fathers opinion, naturally Malcolm or at least Darren. If you think Cassandra is really capable of love, then you'd probably want to try and make things work with Don. As I said, matter of opinion, but me personally?
Team Dreamer. Cute kids, cute home dynamic, adds some female presence to the Dreamer home, and means I can forget about Cassandra, leave her to her life without feeling guilty - I've never been one to kill of Sims because I don't like them. I only kill them to fit to my storylines!

If you want to see the direction I'm sending her in check out my blog http://mypleasantview.blogspot.co.uk/