I watched Heartbreakers and I had fun. I shouldn’t have, considering the film has almost no respect for men, and also decides to end on a really weak note for a caper film. But it had interesting performances, a lot of funny moments, and made me feel really bad about enjoying it. For me, this is a shining example of a guilty pleasure.

We open up with a marriage between Max (Sigourney Weaver) and Dean (Ray Liotta). He’s all too ready to retire for night, with her in tow, so they decide to head to their hotel room almost directly following the reception. Max ends up falling asleep before things proceed further. Dean seems disappointed, but decides to let her rest. In the morning, she’s too sick to do anything, so he heads to his office, a chop shop. Inside, he and his secretary, Page (Jennifer Love Hewitt) end up getting caught in a “suggestive” situation. Max divorces Dean and takes $300,000 in damage for him ruining their few hours of marriage.

We then see the pair getting gas. Page refers to Max as “mother”, and they manage to get their tank filled for free. There’s some tension between the two, with Page wanting to go work on her own, and Max wishing for them to stay as a pair. Their “job” is going around and conning men out of their money by marrying them and then divorcing them as quickly as possible. They average a marriage every three months, so we’re told, although this last con took four. Is Max losing her edge as she gets older? Would Page be more successful if she went on her own? These are questions asked, but unfortunately never answered.

Through a series of events that may or may not be the characters’ own faults, they end up losing all of their money, and end up in debt for over $200,000. They decide to go after a very rich person, and after some debate, they decide upon William Tensey (Gene Hackman), the owner of a tobacco company and also someone who indulges far too frequently in his own product; either he’s smoking a cigarette, or coughing up a lung, never anything else. All the while, Dean has sworn to go after Max for what she did to him, even though he’s not entirely clear on what happened.

So they go after Tensey, or more correctly, Max goes after him. She acquires an adequate Russian accent, and tries to get the billionaire tobacco enthusiast to fall for her. Page is there to set-up situations for them to meet, like when she lays spike-strips down on the road so that his car can no longer be driven, but spends most of her days down on the beach hanging out with a bartender named Jack (Jason Lee). Whether she’s conning him or falling in love, (or both), is something that is revealed later, but she’s going against her mother’s wishes regardless.

Surprisingly, the result from these situations isn’t where the plot ends, although it’s where I’ll stop describing it. Suffice to say that things don’t go exactly as planned, (do they ever?), and that some reconciliation is involved. And so is a statue of a nude man, although it probably won’t take part as you’d expect. Or maybe it will, I’m not a mind reader.

What results are a bunch of humorous scenes and conversations about a smart mother-daughter con team. Ray Liotta’s character shows up again late in the film, and ends up almost stealing the show with some of his one-liners and other scenes. He gives the one real positive speech in the entire film too, which felt a little bit odd, as you usually like having characters figure out their wrong-doings by themselves instead of being directly told.

What I didn’t like was the constant bashing of men in Heartbreakers. There’s a phrase that is said at least once, if not more, that goes “there’s only one man.” It means that all men are the same, and if this film is to be believed, it means that they all think with what’s in their pants. The word “misandry” comes to mind when I think of this film, although this didn’t end with me hating it; it just made me take less enjoyment while watching.

I’m still not sure whose idea it was to team up Sigourney Weaver, who was in her early fifties, and Jennifer Love Hewitt, in her early twenties, and expect them both to appear both desirable to every man they con. But it worked. Somehow. I’m not sure if it’s the costume design, makeup, or because Sigourney Weaver was blessed with amazing genes, but Weaver didn’t look out of place at all acting beside someone thirty years her junior. And no, I’m not saying that Love Hewitt didn’t look good, it’s just that I could believe that a guy could desire both of them, despite the age difference. It’s this point that makes the film slightly believable, which is important to me.

I think that because the situations are clever, the dialogue is sharp, and the actors put in a good effort, Heartbreakers ends up working well enough as a romantic comedy. The simple fact is: I had fun. I laughed for most of the way through it, and I didn’t find myself feeling bored for long, even if the two-hour runtime is too long. There’s enough fun to be had here if you enjoy these kinds of thing, that I think it’s worth watching. I didn’t love it, but it was enjoyable enough to give me a good time, even if I felt ashamed about the experience.