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Okay hi this is an intro post :)
I'm Kaylin, she/her. I'm 27, I'm from Aotearoa and my life was taken over by a middle aged popstar on the 4th of Janurary 2025. This is a sideblog, my main that I like/send asks/follow from is @albertmasonry
Find me elsewhere too!
Here I'm only posting about Robbie Williams and Take That from the 90s to today (sounds like a classic hits radio station)
My original posts include video edits, gifsets, photosets, and sometimes I engage my analysis brain and ramble and take things way too seriously.
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I enjoy being silly in reblog tags. I can't help it. If you prev tags me it's like planting a gold star sticker on my forehead <3
The blog runs on a 24 hour queue. I promise I sleep sometimes
You might call me robsessed
Sometimes robsmacked, perhaps, depending on the day
I am a bisexual Robbie truther and a Leo (in that order)
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Also Mike Stevens
My askbox is always open and you can also dm me any time if you want to talk about our boys or have a request for a gifset or something
‘His relationships with and attitudes about women are something I could talk about another time, I'm still figuring out how to put it into words. But basically: it's a bit odd.’
Oh we need the tea on this because what do you mean odd? It sounds not very good if i’m honest. I actually don’t know of any of his romantic relationships so if you’d be so kind to spill that tea?
Here it is! The long-awaited Jason & Women Post
This has taken me a while to get to because, well, it's Jason. So it's complicated.
This is another long one. tl;dr at the end.
THE RUMOURS
So it goes without saying that there's lot unknown about Jay's personal life.
The only relationships we know about are through sheer luck and celebrity. Meaning, we really only know about them because the women were already in the public eye. He dated Jenny Powell (radio and tv presenter) for 3 years, splitting in 1995. This much we know, as she’s confirmed it herself. Then he was rumoured to date Kathy Lloyd (glamour model) but I don't think that one's true. He was also photographed with Welsh singer Katherine Jenkins at a few events circa 2009 to 2013, and people suspected they may have been together but that probably didn’t happen either.
If he was with anyone else after 1995, I haven't come across anything. Maybe someone else can remember something? But Jay's always been so private I wouldn't be surprised if there was never any evidence.
Then! The only other reported relationship he’s said to have had is with Catherine Tate (as discussed in previous ask) in 2011. The best part is that they met when she was playing him in a video. Were they actually together? The press certainly made it seem that way, and that’s what was reported and hinted at by people who were also at the shoot. They were said to have split because Jason was uncomfortable with the attention they were getting. Though it is also possible that they were just mates the whole time. Either way it’s fun to think about such an unlikely duo out and about together.
Anyway. That's it on public knowledge and celebrities. Other relationships, if they ever happened, he's kept even closer to his chest. So consider the following to be even more unconfirmed. I think he may have been with a Danish girl during the 90s Take That run (also discussed previously) and it may have been off/on. She would have been the one who gave him the ring that he wore on his ring finger for a while which may or may not have had personal significance.
As he notes in a photo caption in Take One (published in 2009): “A Danish girl gave me my ring when we were on promotion… She’s probably married now with seven kids, but we were close for a while.”
So obviously, whoever she was, they kept in touch. And why else would it matter to theorise about her being married if not because they once had a romantic connection?
RELATIONSHIPS: GENERAL
“They [the other members] all had girlfriends.” (Jason, in a 2006 interview)
He said this with the suggestion that he did not have girlfriends in the 90s. Whether the Danish girl thing is true/false, serious/casual, I believe this. His bachelor energy was strong even when he was in his 20s. I think he had his flings and did date now and then, but having an Actual Girlfriend? He might not be the type.
See also: this 2008 Guardian article which is worth a read if you haven't seen it already. When asked if it's easier to get girls when you're a popstar, his response is "I don't think it's any easier. Really. I don't. Put it this way. When I was at the height of my fame, the first time around, I've got five brothers - and at least three of them had many more girlfriends than I did. I was grafting my nuts off on the road, getting a little kiss here, and a little cuddle there, while them [the other lads]… they were sorting women out, left, right and centre."
I think that tells us all we need to know, really.
(From Jackie magazine, April 1993)
"I like sleepin' alone!"
This could mean a number of things. Simply a funny way to answer the question, a matter of peace and adequate sleep, or an honest declaration. He doesn't get the hype. He's a loner who prefers his own company.
"I've never ever once yet found love where I've been totally devoted to one person and not wanted anything else."
This is very interesting. This is 1993. He was only 22. Totally makes sense that he hadn't fallen in love properly yet, that's normal. But he seems to know himself, there's an awareness. This idea of one person. He seems to know that's not something he needs, or maybe can even do.
The Danish girl thing, and any situation he might've had, would be on the low since he was working and traveling so much. Maybe they only met when he was in Denmark. "I love to travel, me" as he now famously once said. Yeah I bet. And the same goes for whatever it was that he had with Jenny. Actual meaningful relationships for any of the boys would have been impossible during the 90s run. When they talk about this part of their lives it’s always with a very casual sense; sneaking girls into hotel rooms, having a girl you only meet when you're in her country, etc. Apart from maybe Howard who did have a steady girlfriend at one point.
I think what may also have also contributed to this lack of serious monogamy was that Jason flirted so much that no girl would see him as a viable option. I also see that behaviour in itself as tied with his insecurity, especially within Take That, of being lesser. But he also could've been lying about not having girlfriends! To protectively hide the truth, or just to make a joke at his own expense and elevate the others. So who knows! But I really do get the sense that he is incredibly guarded as a person, so it makes sense that he's never had a truly serious monogamous relationship because that requires genuine vulnerability.
OBSERVED BEHAVIOUR
Okay but why did I say he was odd about women? Where am I getting bachelor energy from? Especially when he said he wanted to be married?
So the behaviour with women that we can observe of Jay's in the context of Take That (really just interviews, promo, backstage at events, etc.) is the kind of thing you only get away with if you're a hot guy in a band. In both the 90s and the reunion era, if they had a female host or interviewer he was probably trying to flirt with her, sometimes touching her if he close enough. I would like to note though that in all the million hours of TT footage I've watched in the last few months I've never seen him go overboard with it. Enough to make the unwilling uncomfortable? Probably. But he seems good with hints. And again, if he wasn't who he is and looks how he does it would not have gone down that well.
Were his flirty behaviours and attentions successful? Given that we’re just talking about women he met on camera, I doubt it only because there’s not much chance there to meet again after an interview. It’s not completely out of the realm of possibility though. After all, those situations would be some of the only times he could meet women his age and at a comfortable personal level (as opposed to other social situations where intentions are more questionable just because he's Jason from Take That).
In the behind the scenes of the music video for Shine (so, 2006) Jason jokes: “I know it’s tacky, shallow, but working with loads of nice girls just makes a video shoot more pleasurable. I’ve chatted up— I mean chatted to a couple of the girls, yeah.”
This might be a stretch but it almost feels like he's made himself into a caricature of the 'single, flirty popstar' archetype. It's not that he isn't actually interested in all the pretty girls he often finds himself surrounded by, he definitely is, but it's that he plays into the role. It's to the same degree where he would facetiously overemphasise his important to the band, at a time when he had more of a spotlight but still not a lot of shine. It comes back to two things: his insecurity, and his dichotomous nature. The big thing I've found about Jason Orange is he is supremely dichotomous. He IS the flirt, he IS the ladies’ man. But he’s also not. He exists, feels, experiences things in such a way where he is always seeing the other side. He can think two opposing things at the same time. There is no right or wrong about him because he's often both. It's why he was in the band and it's why he left it. And it also extends to how he is with women. He knows the effect he has on them, he knows how to harness it, but does he ever actually utilise it? Or does his insecurity combat his assuredness and prevent him from putting actual heart into it?
CASUAL FLINGS
In a 1996 Smash Hits article, Robbie was asked whether he thinks he could be friends with the boys again and what he says about Jason is: “We were just different as people— I mean, he went celibate for twelve months!”
A year of celibacy. Was this true? An exaggeration? Personally, I think there must've been at least some truth in it for Rob to say it. I think combined with whatever complicated long-distance relationship/s he had or didn't have at the time, his own insecurity, how busy he was, and his own reported ineptitude with women, he probably did have an extended period where he didn't have any sex at all. And knowing him it was probably a conscious choice.
Also, if Rob’s honest experience later in his career is anything to go by, sleeping with groupies isn’t always what it’s cracked up to be. I expect they were probably the only option available a lot of the time, or at least the most accessible. So again it doesn't seem out of character to me for Jason to forgo that.
Then there are the parts of his private life that were exposed by the likes of the daily mail that I will not share here but it's out there. He was photographed on a number of occasions in the early 2010s (so before his formal departure) with what they call "mystery woman" in the headlines. Leaving clubs, waiting for cabs late at night, etc. Basically, they were just women he met or took out on nights out. Is there anything odd about that? No, it's normal behaviour. What is compelling about this detail though, in this discussion for me at least, is that you'd expect him to grow out of it if he was so keen on settling down. He was in his 40s at this point. Again, there's nothing wrong with that, there is no age limit to partying and bachelorism. But for all his intellectualism and being the "deep one" and whatever, if that was all he was doing with women at that time, then it’s likely that he wasn't actually interested in finding someone to have a meaningful relationship with. That's not to say the women he was meeting are not intellectuals or unworthy, but the context of the city bar/club scene means that aspect was not a priority. With only some exceptions, you don't tend to chat to a girl at a club and take her home because you think you’re going to marry her.
From the 1995 Take That annual: “I have to hold back from developing any strong feelings for a girl. I get attached very easily but because of my job I have to hold back. Just keep it nice and casual, that’s my rule.”
He's in control of his feelings. Maybe too tightly controlled.
1996 German interview: “That was my girlfriend that particular day.”
This is a mysterious little segment (timestamped link here) and there's more to it than that one line. Have a watch yourself and see what you make of it. What I really see in it is a resistance to labels, his casual nature, and a disregard of the whole notion to make him seem available. He's also suggestive with the female interviewer in the manner discussed in the previous section.
FURTHER COMPLEXITY
(Jason's answers to a Cosmo-like sex-themed questionnaire, 1994)
A very strange but interesting read. The answer that stands out to me in regards to this discussion is to the "what's the difference between love and lust?" question. Jason says "women and men"
It tells us a lot about his feelings. It's almost as if he's outright assuming that men do not experience love, likely because he'd never been in love himself. Though he does, in true Jason fashion, highlight the less sexualised attributes of a woman's eyes, personality, and attitude.
Bringing up that 2008 Guardian article again: the author notes that Jason is "single and inclined to say things like (when I ask if he fancies any of Girls Aloud): 'Only in as much as I fancy all girls, all the time.' But then he says he wants a wife and babies, because that's the whole point, isn't it?"
His attitude just circles around and around.
In a 2006 Spanish interview Jason says "I don't want to lose the choice of being a father. But to me it's sort of a huge responsibility, which I'm not sure I'm ready for yet. I'm only 36!"
Clearly, he's hesitant to commit. He still romanticises fatherhood and hopes to settle down, but the reality of doing so is also obvious to him so he's overthinking. We'll come back to this in a bit. Not being ready is also a theme.
In that one 2007 interview in Taiwan where the boys were encouraged to ask each other questions, Howard asked Jason: "When are you going to get a girlfriend? Or why are you not ready for a girlfriend?"
The others chime in agreement, that he's "not ready", so this must be the excuse he’s told them. It also insinuates that at that time he'd been single for a while.
His response?
"I'd love to know the answer to that. I don't know the answer. I just ain't ready. I'm self-developing. I've got issues I'm working out.”
I think it’s admirable that he was aware of this, but saying it is just the easiest way of not addressing the real reasons. He knew he couldn’t be a good boyfriend to anyone because of the personal issues he was dealing with. I imagine a lot of it had to do with being in the band. As previously discussed in the Orange Tea post, he’d always been uncomfortable in his career and what it all meant, the fame included. I think he may have also been coming to terms with the type of person he is; i.e questioning if he is actually well-disposed to the traditional monogamous arrangement expected of him. For someone who values freedom so much, the prospect of being locked down to a theoretical person was probably scary. It's also a huge responsibility, as he said so himself. So maybe the “I’m just not ready” excuse was just a way to not have to deal with those questions, both from others and within himself. I see parallels too with Rob, who had expressed the same thing. He had his demons and issues and before he met Ayda he had decided to not put all that he is on another person, essentially closing himself off from a serious relationship. But then he met the woman who would become his wife and that changed. With Jason, however, I don’t think he has the same romantic ideals that Rob had and it wouldn’t be so easy to convince him to settle down. Also a big reason why it worked out for Rob and Ayda was because she was there for him when he was at a really low point, and I just can’t imagine Jason succumbing to such a period and letting a woman in God forbid. It’s just not fathomable.
TL;DR
My interpretation of all this is that it would take a miracle for Jason to settle down with someone. He's given it a go, but I think at the end of the day he's just not suited to it, or that's what he believes at least. Everything I know about this man can be boiled down to one thing: he’s an over-thinker. He understands the weight of commitment, and he’s created a barrier for himself to not have to ever deal with it. Because being in love and having a family is all lovely in theory, he dreamt of it, but for an over-thinker the reality of it all is actually pretty terrifying. Most people just take a leap of faith and do it anyway because it’s what people do, but Jason’s barrier locked him out of trying.
The other big part of all this is the simplest: he hasn’t met the right person. Again, he’s an over-thinker and probably had a lot of expectations when it came to finding his match.
Now that he's in his 50s does he still date? Have hookups? It's possible. But I think he's far more focused on his family, his mates, his work, just living his life freely. And now that he's an aging ex-popstar I'd expect he's toned down the flirting. Only a bit, mind. His is not a rizz you can let go of so easily.
"I remember a couple of times I was in the ocean, and off in the distance I could see dolphins swimming, off in the background. And I think, cos I had the tattoo, I felt I could talk to them."