. from new york city, this is "nightline" with dan abrams. good evening, thank you for joining us, many say that when you meet that special someone you just know. and some might even say the same applies when picking out that

special ring. but there is a lot more to choosing a diamond than meets the eye. and underneath the surface, these precious stones may not always mean what they seem. my colleague went undercover to investigate. >> reporter: my wedding was the best day of my life, the setting beautiful, and the bride, a clearly out of my league doctor named bianca looked uncomfortable and hot. the only stressful experience was buying the perfect engagement ring, think about this, this is probably the most emotional purchase of your life. so how do you know if you're really getting what you think you're buying? >> looks like i'm a waiter at tgi fridays. >> or an undercover car salesman. >> reporter: to see how up front the dealers are, i have

reluctantly agreed to wear a disguise, so i can go undercover as a bachelor on the hunt for a ring. >> are they making a sequel to the vampire slayer? you know, more importantly, somebody is not going to buy a diamond ring like a bear trap. i feel like i need a beret. >> reporter: for our undercover shopping tips, our producer, erin, will play my girlfriend. she will wear a hidden camera. and this one will play the role of my supportive mom. she will wear a camera, too. she is actually an international renowned gem and jewelry expert. she told me something that everybody should be aware of. it goes by the name of clarity enhancement through fracture filling. here is what it is, they take a

desirable stone that has naturally occurring cracks in it, and with high tech laser they fill the cracks in. they disappear to the naked eye. the stone becomes more attractive and looks like a higher grade diamond. >> looks like a great diamond. >> it is, it is a beautiful diamond at first glance. >> reporter: these fixed up diamonds typically sell for 30% less than comparable untreated diamonds. >> there is nothing wrong with that, i know people that want more bang for the buck. >> reporter: but there is a problem, sometimes sellers don't always explain what it is and why it seems you're getting a discount. >> unfortunately, there are jewellers who sell them without disclosure. in the gem and jewelry field, we say in gems, you get what you pay for or less. >> reporter: so we have decided to test how open dealers are about this. our destination is new york

city's fabled diamond district, the country's largest marketplace for diamonds. >> hi, how are you? >> reporter: this is a shop called "diamonds usa". >> that is a real mustache. >> reporter: my undercover mom has already told alex here about our are three grand budget and interest in something around one carat. >> the color, and more clarity. >> reporter: i notice on the paper holder it says clarity enhancement. >> i'll give you the certificate with it. >> reporter: no mention of clarity enhancement. so i asked directly. what is clarity enhancement? this is a key moment right here, what will alex say? >> that is the polishing of the stone. >> reporter: wait a minute, that is not at all what clarity enhancement is, but alex moves right off the topic. >> you have the symmetry. >> reporter: i ask him, why is

it such a good deal? >> don't judge the price, i'm giving you a really good price for a nice stone. >> reporter: anything i should know about the special care for this? clarity enhanced diamonds may not withstand repairs with high heat. >> nothing we should know about it, though? nothing we should be worried about? >> don't be worried about anything. >> reporter: so i fork over the cash, and later alex brings a certificate and a $9700 appraisal, which makes the diamond look like an even bigger bargain. we head back to the studio. >> and the ring does look beautiful. down here it says feather filled. grades are based on appearance after clarity enhancement. now feather is another word for crack or fracture. and here it says filled. doesn't say with what. >> reporter: to find out exactly what is inside our brand-new

diamond, we take it to an independent lab for analysis. here, an x-ray technology determines the composition. >> it has been clarity enhanced. if it was not fissure filled, it probably would have been more down in the imperfect range. >> reporter: the tests show it is filled with high tech glass. now it is time to go back to the store in disguise and to see what they have to say and to reveal who we are. we tell alex the results of our independent testing. >> it says clarity enhancement is filling the cracks with glass that is basically lessor owe is -- is that not the case with this stone, you don't know what clarity enhancement is? >> no, i know what it is. the polishing of the design. >> reporter: it is time to tell them who we are. remember i was here last time without the mustache. you're right, this is totally

fake. this is not my mom, she is a gem expert. and we had this looked at by experts and it is fracture filled. i asked you what is clarity enhancement. >> i said it is a polishing process. no one even told me -- >> reporter: you really don't know what clarity enhancement is. >> no, i know it is a polishing enhancement. >> reporter: sounds to me you don't really understand what you're selling? >> from what i know, it is included in the packaging -- >> reporter: but this is work that is done on the internal part. >> that is what i'm saying, that is polished, polished inside. >> reporter: we know you're saying it is polished inside, but that is different. >> i did say it was polished. >> reporter: this is one of the most emotional purchases a man will make in his life. don't you have a special responsibility to tell me everything about the stone. >> there are many people that know that they're buying the enhanced stone. >> reporter: and then the owner

joins in. >> i clearly didn't know it was enhanced. i asked you. >> you have it on camera before. as a matter of fact, i do. >> reporter: after we show the video, he tells us about the risk. >> i wanted to go get the thing refitted or re-sized and they used a lot of heat on it. >> they put direct heat on it. >> but i was never warned about it. >> if you want your money back, we'll give you your money back, we'll write you a check. we're not doing anything to misrepresent you. maybe it was a misunderstanding. >> reporter: but when i asked whether he thinks the sale was deceptive, he gets angry. >> don't take my picture, please, don't take my picture, talk to me like i'm a man, please. >> reporter: i need the property back. >> i know it is your property. >> reporter: if you want us to leave, we'll leave. >> no, you came like in good faith. we're trying to be like in good faith. >> going forward -- explaining

o -- >> i'll tell them -- >> reporter: in the end, he offers our money back and offers to help us find a new diamond. >> but you see, we're all still friends, sorry about the -- >> reporter: thank you, i'm happy to be rid of that. for "nightline," this is dan harris, in new york. now experts tell us the price we paid was a fair price for a clarity enhanced diamond. we spoke to the owner today and he told us today that the clarity enhanced diamonds were a good choice for people with a choice like we had. and he is proud of his business. and speaking of budgets, come on, dan, you couldn't have done better with the mustache? next, we're going on a hunt with some bona fide extreme cougars. abc news "nightline," brought to you by macy's. how do you do a summer clearance event the dodge way?

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i learned today that a cougar is defined as a middle aged woman who dates men at least eight years younger. and this only applies to women why? i digress. they're sexy, they're powerful and seem to know just what they want. but what about the objects of their affection? to examine these relationships, we're looking at the positively animalistic world of these cougars and cubs. >> reporter: thursday night on the sunset strip, kathy newman

is on the prowl. so this is your hangout? the rainbow room, next to the roxy has been here for years, so has kathy. she is one of the stars of tlc's extreme cougar. >> i am not the kind of woman you take home to meet your mom. >> reporter: she is 55, her boyfriend is considerably younger, i'm 55, he is 25. >> reporter: more than half your age? yeah. >> how about another round now. >> reporter: that is a pretty big difference. >> yeah, it is, but it doesn't bother me. >> reporter: the show also features a couple from chicago. >> my name is sherry winkleman and i am 50 years old, and there are 24 years between desmond and i. i have dated younger men before, i am a serial cougar. >> reporter: the show plays to that timeless theme of older

women and younger guys, and if you think we've made progress since "the graduate," don't you think we've made progress since harold first fell in love with maude? think again. >> you know it doesn't work, when you get later in life, you're 70, he is 50. sure, come on. >> reporter: sure, the older man, younger woman is much more common and much more accepted. shows like cougartown celebrate it. but there is still a stigma attached. does it bother you being called a cougar, being in a show called "extreme cougars"? >> yeah, if i think about it. >> reporter: it does bother you? >> yeah, it is a weird term. and extreme cougar is like extreme, like you're a gilf, not a milf. this is graduating, going into another -- another you know level of existence here.

>> reporter: kathy's toughest moment on the show comes when it is time to meet the boyfriend's family. >> your grandmother is cool. >> that is because she is your age. >> reporter: in chicago, sherry you wingelman had a similar encounter with desmond's mother. >> whoa! >> reporter: by the looks on their faces, they're shocked. puzzled. you get the sense that the facts that they're an interracial couple they could accept. but this? this is something else. >> she is a very special person in my life. and i love you. and i just wanted you to know. >> reporter: his family be damned! >> it has restored my faith my men and what they're capable of giving women. i wouldn't have traded it for

anything, even if it ended tomorrow. >> okay, nice meeting you. >> reporter: what a contrast, kathy and brad, whose relationship pretty much ended as soon as they walked out the door. >> how long after the reality show did you break up? >> not long. yeah. >> i think right there. >> really? >> yeah. that was dessert. >> reporter: what happened? what happened between you guys? >> ask him, i don't know. >> reporter: he says basically it is not you, it is me. break-up 101. >> i'm never going to be the person you want and are looking for. do you buy that? >> i don't know. >> reporter: that is the thing about extreme cougars, you totally get what the older person is after, the fountain of youth, right? but the younger guy, what does he get out of this. >> reporter: how many older women have you dated? >> actually just one of them.

actually, she was my new year's kiss two years ago. and she was just a banging milf. >> reporter: what did he see in her? >> she is just a sweetheart, look at her, how could you not like her. >> reporter: but in keeping with the couple's therapy, the doctor has some theories. what would those be? >> well, that fundamentally, we -- men want our mothers. >> that is not true at all. >> reporter: never mind she has a son about his age. she has moved on. back at the rainbow room on sunset, kathy is much in demand. truth be told, she doesn't need my help at this game she is a top gun. >> your first time here? what do you think? >> i love it. >> reporter: oddly riveting to watch, that is exactly what tlc's extreme cougar watch is

banking on. i still don't know if i have a handle between the true difference between cougar and extreme cougar. but i am certain that can be answered by watching extreme cougar wives, which premieres on tlc wednesday august the 14th. next, the votes are in. and you can't hold us from announcing the winner of our summer song. this is not a safe thing to do. be careful babe. there should be some way to make it easier [ doorbell rings ] let's open it up and see what's cookin'. oh i like that. look at this it's got a handle on it. i don't have to climb up. this yellow part up here really catches a lot of the dust. did you notice how clean it looks? morty are you listening? morty? [ morty ] i'm listening! i want you to know the only thing anyone really cares about is that first day.

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oprah gets dissed at a fancy swiss shop, and a world record setting for getting hitched. on tonight's feed frenzy. >> a weird decision, oprah has a higher net worth than many in the country, but a shop clerk that didn't recognize her apparently determined she just didn't have the cash for a pricey bag. oprah stopped into the shop. >> she said you don't want to see that one, you want to see

this one, it will cost too much, you can't afford it. >> the billionaire says that shows even she can still be a victim of racism. the store's owner says it was just a misunderstanding. mile high club, talk about setting a high bar. they had a chance to go on a honey moon and break a world record? they were charged hundreds by the fiji airlines to break the highest numbers. when they landed they began all-expense paid honeymoons on the beautiful fiji islands. they will be tough to top. the envelope, please, the winner of our song of summer won by a landslide. did you vote for we can't stop? or can't hold us? maybe, but one tune drowned out all the others. blurred lines. almost impossible to listen to without a little shimmy and a

shake. happy summer, everybody. thank you for watching abc news, tune into good morning america tomorrow. good nig "omg! insider," the top trending stories you need to know. >> this is ridiculous. >> usher's ex breaks down. her custody fight after their son's near drowning. >> my son nearly die on the scene. amanda bynes forced to stay in a psych ward. then, leah remini raising the stakes, filing a police report. >> i do feel compelled to help families that have been destroyed. plus, expendables after bruce quit. plus, he survived extremely weight loss. >> i'm not sure we'll be able to do this. >> remembering whitney on her 50th birthday. houston's new tombstone.

and the beatles of broadway backstage with a look-alike. for 24/7 access to celebrity news, "omg! insider." usher fighting for his kids. amanda bynes facing another setback. i'm kevin frazier. >> our reporters are there as amanda bynes's parents are in court again today and usher goes in front of a judge to prove that he's a fit parent. >> we focus on amanda and usher and their crucial legal turning point. >> i don't know that my son is going to be 100% the way he was before this incident. i don't know that. i have no proof of that. a so called emergency. it is very much an emergency. >> usher's ex in tears today. overwhelmed with emotion and breaking down on the stand. >> i know this is very difficult. >> it's ridiculous. this is