01:06:35.480welcome to the show sean how's it going hey it's going well pearl uh so yeah i mean the topic is
01:06:51.080like dating women over 50 uh i have twice actually okay one back in 2014 and that was kind of like
01:06:59.440free dating apps and things like that i happened to meet her at like a whole foods okay and she
01:07:05.560looked pretty good to be honest like she kept in shape like she she did all the maintenance that
01:07:10.420maybe you see let's say older women in new york city as an example who tend to like really keep
01:07:16.120in good shape uh like compared to like the rest of the country so she looked pretty good for her age
01:07:20.500i would say uh but she was primarily looking for fun if that made sense like usually when older
01:07:26.700women are dating younger men they're not looking for anything like long-term or serious so we dated
01:07:32.460for a few months uh it looked like she was just looking for you know someone servicing her car
01:07:38.100we'll just call it uh and that was pretty much it and how old were you at the time uh i was 24
01:07:45.200so she was probably I want to say around 54 55 she was divorced she had kids around my age
01:07:53.480her husband was out of the picture he went to jail for some sort of like financial crimes
01:07:58.180and so he's kind of out of the picture so that was kind of how that ended up and then I dated
01:08:06.840another woman in her 50s this was about a few years ago before I met my current girlfriend
01:08:12.580and similarly she had kids around my age uh but what I noticed was she was way more entitled
01:08:20.080uh she kind of had that sort of like mentality of like the reason she divorced her husband was
01:08:26.320because he felt like he was not ambitious enough and she could kind of do better uh and then I
01:08:31.020guess post-divorce she's just like meeting guys on the apps just kind of like having a lot of fun
01:08:35.940if that makes sense with a bunch of different guys and so kind of seeing how it's affected women
01:08:40.500post social media post you know dating apps coming out I think the behavior has now changed
01:08:47.160to hook up with as many guys as possible they're not necessarily looking for relationships as they
01:08:54.180may claim they are at least the one that I experienced was like that okay so neither of
01:09:00.640them were looking for relationships they both just wanted to have fun but you it sounds like
01:09:04.880you're saying the second one was a little crazier maybe like she seems yeah she was definitely
01:09:09.240crazier definitely more entitled and i think that's i think that behavior is now more the norm uh
01:09:15.480post social media post smartphones and things like that coming out um they may have been looking for
01:09:21.480something long term but it might just not have been with let's say guys my age yeah uh so that's
01:09:27.320where i would kind of put them in that that sort of bucket got it got it well thanks for telling
01:09:32.520me about your experience sean i'm gonna take the next caller that's good thanks pearl thanks
01:09:39.240okay we got uh ck next are you good to be on camera thumbs up if you're good good thanks girl
01:09:46.280thanks okay we got uh ck next are you good to be on i think someone's echoing uh can you hear me
01:09:54.920all right yeah can you turn off the show in the background yeah my fault sorry about that it's
01:10:01.000okay are you good to be on camera i'd actually rather not be on camera if that's all right
01:10:05.960okay that's fine um so women in their 50s um how many of you dated yeah so i did this one time i
01:10:16.760have one experience um and it's actually similar i think to the last caller um where i was in my
01:10:24.680early 20s and i tried dating someone that was um i think she was actually 49 when i met her but she
01:10:31.960turned 50 um the time in the time that we were together and did she want something serious i'm
01:10:38.680guessing not if you're in your 20s what's interesting is i would probably say yes but
01:10:45.880i don't know it seemed like her actions weren't really in alignment or like she didn't know how to
01:10:52.440go about something serious um to be honest i for me it was just a different scenario where
01:10:59.400she came on very strong um she was never married no kids um it was kind of a weird situation lived
01:11:05.960alone had like a beautiful condo and i was when i was in my early 20s it was like oh cool like you
01:11:12.040know it was almost like you know she saw like a motherly role and kind of hopped in as weird as
01:11:18.840that sounds but i know that she obviously wanted something in return and it got very toxic very
01:11:25.720fast. It was definitely my worst relationship and the one that, you know, I had a lot of hard
01:11:32.660learning lessons from, I'll say. Why was it your worst relationship? Like, what went toxic?
01:11:39.920Wow, that's a great question. So, I had been in a couple other relationships just kind of
01:11:45.340throughout college and high school, and they were all very, you know, just very, in my opinion,
01:11:52.320just normal relationships um but this one it almost felt like she had and it kind of came
01:11:58.720out at the end where she's worded it this way but she had a lot of trauma and baggage from
01:12:03.920a lot of her dating life um she had been single for i think about almost 20 years i think it was
01:12:11.440like her early 30s where like her engagement got cut off um but she was living you know the fun
01:12:17.280single life um in a big city she was very well off financially and also a very attractive woman
01:12:23.520um so it was like kind of fun something i joked around with with my friends at the time but it
01:12:28.880quickly became like more and more demands more and more that she wanted to see me um i had her
01:12:34.480do some of the craziest things um she would throw things at me when she was angry and things just
01:12:39.760kept escalating very quickly and then i knew i had to get myself out of here she also contacted
01:12:45.120um when i had left one time because she was acting crazy she had like contacted my sister
01:12:51.140like it was like stuff i had never seen before just like saying like the craziest things all
01:12:57.260the time and doing crazy and she was like your mom's i'd imagine she's like close to your mom's
01:13:02.780age at that point right yeah at that point my my mom was only like i think five years older than
01:13:07.620her so um i mean when i look back on it now it's kind of like obviously i'm the i'm the dummy but
01:13:14.540But I do think that, you know, just the fact that she had been single for so long and she talked a lot about her traumas.
01:13:21.540You know, she she was just getting she had gotten used, I think, to like dating guys that were well out of her league that would never take her serious.
01:13:30.000And I guess she was just never really to able to land a guy that she could truly respect.
01:13:34.760So I guess she kind of she got some type of rush, I think, going after a younger guy.
01:13:40.640i'm curious what kind of stories did she tell you about being single in the city like
01:13:46.280was she seeing other guys too or was she only seeing you yeah no so it's it's interesting like
01:13:53.180so during the first few months um well she always lied about it i'll say i did eventually like kind
01:14:00.140of find out that she was seeing other guys and then that's when she kind of backed me into a
01:14:03.960corner and was like kind of turned it back on me and was like hey if you basically don't commit to
01:14:10.200me um you know i am going to continue to see other guys like i didn't know kind of thing um so at
01:14:17.820that time you know i just i i remember i was busy kind of just starting in my career and i got
01:14:23.300uncomfortable you know with with with her and i was like yeah whatever that's fine i really wasn't
01:14:27.760seeing other girls so i just uh i took her up on it and uh yeah i mean she she just eventually
01:14:35.180opened up about more and more things um and then it just was very evident that she had been with
01:14:40.140guys um like for example she used to date a guy that played in the mlb professional athletes just
01:14:46.000guys that you can tell never really took her serious as for how highly she thought of them
01:14:51.600um and this was when she was in her 30s so it had been it had been quite some time got it so she had
01:14:57.920dated guys in the major league baseball how cute do you think she was when she was younger like
01:15:03.200one to ten yeah she was uh to be honest i would say like up until because i had seen pictures of
01:15:10.500her when she was like in her late 20s i would say she was like definitely above an eight like a
01:15:15.280really a true eight probably eight and a half um and that's and i'm very conservative i i would not
01:15:20.860give uh really a lot of girls um an eight like for example a woman like madison beer i know that
01:15:27.220people freak out about i would give like a nine so she was definitely up there yeah um
01:15:33.180um so she just stayed in what city was it uh yeah it was in uh baltimore baltimore maryland
01:15:41.280and did she stay in that city or had she moved from city to city
01:15:44.840she she actually was in a city before that she was out in uh san francisco and then she had moved to
01:15:52.220baltimore um i believe after her engagement broke off yeah i find that like the eight pluses go to
01:15:59.540a big city and then move to a smaller one when they age out so I was just kind of curious if she
01:16:04.540had the same life cycle yeah seems like that it was uh it was definitely eye-opening yeah
01:16:11.000what what did she do to afford that lifestyle yeah that's what's interesting and I never really
01:16:17.940was able to wrap my my mind around it um she I guess long story short she was and this is going
01:16:26.840to sound crazy, but she was an executive assistant. I did eventually kind of figure out which company
01:16:31.800she worked for. She never really talked much about it, but I do know her boss was very high
01:16:38.920up there in terms of what he did. So I assume he just paid her well. I don't know too much about
01:16:44.220that though. Got it. Cool. So is that your only experience dating a 50 plus woman or a woman that
01:16:52.060old yeah for the most part i would say in terms of dating i've had my fun here and there um but
01:16:59.740yeah definitely after that experience it was like i i'm gonna be honest i think the longer they go
01:17:06.540single it's the the worst worst of a deal you're gonna get to be honest and eventually all of that
01:17:13.500trauma all of that um just poor decisions honestly for for many decades just kind of gets dumped in
01:17:21.180on you by the time you hit 50 and then you try to attach with a woman like that so yeah well tell
01:17:27.820her if you if you talk to her tell her to call in i'm curious about her life so yeah no definitely
01:17:34.300and uh thanks for bringing me up pearl yeah thanks for coming yep take care
01:17:40.540okay i think that's all of them i know there's some if they're saying the zoom isn't working
01:17:47.100on the website i don't know why we'll look into it for next show um we i don't know it's
01:17:56.300being over 60. does fishing count as dating over 65. well thanks for guys for sharing your stories
01:18:02.460i always want to hear you guys's experiences dating and um ladies over 50 good luck i wish
01:18:12.540you well like the video on your way out guys subscribe to the channel and if you want if some
01:18:18.220nala apologists want to apologize to me in my twitter space it's tonight at 10 30.
01:18:24.620sorry 9 30 central um and i'll see you guys later bye