CONTENT creator Tiffany often visits retirement homes to make videos with older men, but she had no idea that she'd end up falling in love with one of the residents, Jim. He told Love Don't Judge: "I saw her and I thought, is this the new Marilyn Monroe?" Speaking about their connection, Tiffany added: "I was like this guy is so funny. We just have a really nice bond, maybe because it's because I didn't have a grandfather in my life." The couple's 42-year age gap has been met with a fair amount of criticism. "We get a lot of hate on the internet, they will tell me that I'm a gold-digger, that he's my dad, that I'm using him for views," Tiffany explained. Jim added: "We're not hurting anybody. We're making a lot of people envious." In this episode of Love Don't Judge, the couple will be sitting down with Tiffany's friends, Samantha and Ryan, to find out what they really think about the relationship. Speaking sincerely, Samantha revealed: "Honestly, I was pretty shocked at the age gap. He's like twice our age, Tiff."
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00:00If he was my dad, would I be doing this?
00:04I'm Tiffany.
00:05I'm Captain Jim.
00:06I pick up men at retirement homes, and now I'm with one.
00:09A younger woman is an older man's jewel.
00:11We get so much judgment for it.
00:13How much do you charge?
00:15He's on his way out soon, by the sounds of it.
00:17Where's this guy's family? Someone needs to step in.
00:20Absolute filth.
00:22So my friends, Samantha and Ryan, are coming over.
00:24They haven't really met him.
00:26They've only seen him on the internet.
00:28It is crazy.
00:30Honestly, he's like twice our age, Tiff.
00:34If it's for money, there's other ways.
00:35Stop!
00:36What if he just dies?
00:40Exercise is important, honey.
00:43Oh, God, these old bones.
00:45I'm about a year and a half away from 80.
00:47I hope I can get up.
00:48And she's 42 years younger than me.
00:51We met at the retirement home.
00:53Retirement community.
00:55She keeps calling it a retirement home.
00:57That's a retirement community.
00:58I'm known for filming with older men.
01:01And I got to talking with him, and he asked what I did for work.
01:05And I told him.
01:06And I asked if he wanted to be in a film with me,
01:09and he said he did.
01:10So the rest is history.
01:12I saw her, and I thought, is this the new Marilyn Monroe?
01:15You know, the Kennys had, you know, Marilyn.
01:18I got Wisconsin Tiff.
01:21I formed an attraction to him after he started
01:25doing the role plays with me.
01:27And because he was so good at doing them,
01:29I'm like, this guy is so funny.
01:31We just have a really nice bond.
01:33Maybe it's because I didn't have a grandfather in my life.
01:36And I get that.
01:39It sounds so wrong, but I mean, I really do connect with him.
01:42We are going to Vegas in a few days.
01:45Because of my work, I am going to be filming with,
01:50I can't believe I'm going to say this.
01:52I'm going to be filming with 20 guys.
01:57So he supports my work and everything,
01:59so I'm very thankful for that.
02:00My biggest thing, just don't be deceitful.
02:03Be honest about what you're doing.
02:04Yeah.
02:05And she is.
02:06Yep, I'm very honest with what I do.
02:07And I'm proud of it.
02:08It is what it is.
02:09And he gives me my space, because we
02:11don't even live together.
02:13It's nice, though.
02:14It's really nice, because when we do see each other,
02:16we value that time together.
02:18They say there's the three rings of marriage.
02:20I don't know if you've ever heard of them.
02:22There's the engagement ring.
02:24Then there's the wedding ring.
02:26And then there's the suffering.
02:32Hopefully that won't happen with Wisconsin kids.
02:33We have not had any problems, so.
02:35No, it's true.
02:36We really.
02:37Yeah, we're like best friends.
02:38Right.
02:38We view our relationship as an open relationship,
02:42especially because of my job.
02:44And I honestly don't care if he goes on dates with other people.
02:48But at the end of the day, I know he's coming back to me.
02:50I love when you wear those cotton summer dresses,
02:54because it accentuates your body.
02:56Yeah.
02:57When I'm with guys who are my age or even younger than me,
03:01they're all like, go, go, go, go, go.
03:03And they just love bombing me.
03:05And it's just too much.
03:07So when I'm with older men, it's just
03:08a whole different ballgame.
03:10I love that I don't feel like I have to prove myself.
03:15We get a lot of hate on the internet.
03:17They will tell me that I'm a gold digger, that he's my dad,
03:20that I'm using him for views.
03:23I mean, technically, I mean, what I do for work,
03:26I mean, that's what you do.
03:27You get views on the internet.
03:28I don't really feed into it, because at the end of the day,
03:31I mean, he's happy.
03:33So that's all that matters.
03:34So many people think that he's my dad.
03:37If he was my dad, would I be doing this?
03:45Not her dad.
03:46People will still think you're my dad, even after doing that.
03:51We're not hurting anybody.
03:52Nope, we're not.
03:53We're only hurting their eyes.
03:54Yeah, we're consulting adults, and we're
03:57making a lot of people envious.
03:58Somebody said, oops, he fell down
04:00the stairs the same evening.
04:02I know his kids and grandkids are not happy.
04:07And I go, he doesn't have any yet.
04:10Is this the father of Donald Trump, or what?
04:12Donald and I are the same age.
04:14Shame on her for doing exactly what I would do.
04:17I should go find someone my own age.
04:19Or they say nobody wants me my own age,
04:22and that's why I'm with older men,
04:23because that's my only options.
04:25Or it's usually a lot of the hate comments
04:28are coming from younger men.
04:29How much do you charge?
04:31He's on his way out soon, by the sounds of it.
04:33Cash is on that creepy old man, girl.
04:36Ugh, gold digger.
04:37Wonder what her thoughts would be if this was happening
04:41with her granddad.
04:42Absolute filth.
04:43Where's this guy's family?
04:45Someone needs to step in.
04:47Somebody said, this is elder abuse.
04:50If this is elder abuse, bring more on.
04:52I think.
04:53I can't keep my hands off you.
04:56You know, it's like putting out a steak
05:00and there's a hungry dog around.
05:02So my friends, okay.
05:05So my friends, Samantha and Ryan, are coming over.
05:08They're gonna share their opinions on our relationship.
05:11It's gonna be interesting to hear
05:12what they have to say about us,
05:14because they haven't really met him.
05:16They've only seen him on the internet.
05:18It is crazy.
05:20Honestly, I don't even understand.
05:23We love Tiff, but it seems very, very strange.
05:26She could be doing it for the money.
05:28I think she might be.
05:29I'd say it, but what's she gonna do if he dies?
05:33So what did you think of when you found out
05:36about our relationship?
05:38Honestly, I was pretty shocked at the age gap.
05:44He's like twice our age, Tiff.
05:48Aren't you worried about people thinking
05:49that you're kind of being a gold digger?
05:52Really?
05:53Like, that's what everybody else is thinking.
05:56I am actually really surprised that you said that
05:59because of our work and how close we've come together.
06:03I can't believe that you're actually saying gold digger.
06:05It's an honest concern of mine.
06:08Like, I feel like this is past just work at this point.
06:12Okay, so him and I have a really strong relationship
06:17and it's not just about money.
06:19Yeah, obviously there's money involved,
06:22but I really do like him a lot
06:24and I don't see what the problem is.
06:26I mean, I understand you don't understand it,
06:29but we are like this when we're together.
06:33So he makes you happy?
06:35Yeah, yeah.
06:37I mean, it seems a little strange, Tiff,
06:40and I don't mean to go back on that,
06:42but if it's for money, there's other ways.
06:45Jim, you seem like a nice guy.
06:47I don't mean to be rude or anything like that, but...
06:50No offense.
06:51Money?
06:52Yeah, it just seems a little strange.
06:53I probably make more than him.
06:55Are you running out or is there...
06:57No, why would you say that?
06:59I'm just curious.
07:00If you guys are... Stop.
07:02I'm going out and getting another life insurance policy.
07:04Oh, you must be really happy then.
07:06Well, I mean, we have to keep each other protected,
07:08so you just never know.
07:09He is getting older.
07:10So it was actually his idea
07:13to do the life insurance stuff for me.
07:16Since you guys did bring that up,
07:17I didn't want to be morbid, but are you worried?
07:19Like, he's 45 years old and you're...
07:21Are you worried about him dying?
07:23What if he just dies?
07:24I would be really sad, honestly.
07:27I mean, I don't really think about it
07:28because all that matters is that he is happy
07:32during his last final days,
07:33and I bring him so much joy, so it is worth it.
07:37I mean, regardless of what people think.
07:39I'm so sorry, Jim, but you are getting older
07:43and you love me being around you,
07:45and regardless of how many days you have left,
07:48for all we know, you could live to 105.
07:49Jim, are you okay with Tiff's career
07:52and her just to be blunt, sleeping with other men?
07:57I gotta admit, it took a little getting used to, you know,
08:00but, you know, that old saying,
08:03a man's gotta do what a man's gotta do?
08:06Yeah.
08:07A woman's gotta do what a woman's gotta do,
08:08and she does it, so I'm kind of excited.
08:10Yeah, it's...
08:11If I don't accept it, I lose it.
08:13No.
08:14So you're kind of forced to?
08:16No, forced isn't the right word, it's...
08:21It's an option that I can either choose or not choose,
08:24and I say, go away.
08:25Okay.
08:26But does it take a pang at my heart
08:28when I see her in these videos sometimes?
08:33Yeah, sure.
08:37It's definitely different and hard for me to stand behind,
08:40but if you guys really make each other happy,
08:43like you seem to, I'm not going to hate you for it.
08:48I've tried dating older women, women my age,
08:51and it's probably gonna tick off
08:53some of the older women out there,
08:54but I'm sorry, you use your mojo a lot, you know?
08:59They hit that 50 mark or whatever,
09:01and it's like, I don't know what happens.
09:04And it's not just physically, it's mentally.
09:07So a lot of people say,
09:08well, why do guys want to go with younger women?
09:13Their mojo is still on.
09:14I love Jim the most because of his money.
09:16Just kidding.
09:20I love his personality.
09:22When we're together, we connect on a deeper level.
09:25Tiff thinks she's never going to get old.
09:27I'm not.
09:28Since I am old, I'm trying to warn her that, you know,
09:33you're still in your 30s, but you don't know what's coming.
09:36There's surgery that can fix that.
09:38The day may be over for me soon, but.
09:41Not for me.
09:43So my message to everyone is,
09:45live your life while you can,
09:46because time is more valuable than money
09:49and everything else.
09:49And that's why I got this honey money, yeah!
09:52Yeah!