Hollywood celebrities are known for dating around and having multiple relationships, but one celebrity who has had a long list of memorable relationships with a lot of famous guys would have to be Taylor Swift. Her list of ex-boyfriends is very interesting due to the fact that she has written songs about a lot of the relationships that she has been in!

Swift is obviously someone who lives her life for love and has experienced the ups and downs of various romances over the course of her career. Some of her exes have actually spoken up and revealed what it was like to be in a relationship with her.

Updated October 2023: Taylor Swift has dated some of Hollywood's who's who. While those who date her know that they may be the subject of one of Swift's songs in the future, many take the chance to date her. After all, by all accounts, she is a lovely person to be around.

While not all the men that Swift has dated have made comments about her after they have broken up, others have. Some of the comments are kind, others not so much. It appears to be based on whether Swift and her ex have been able to split on good terms how the comments fall. That is, save for Joe Alwyn, who has said nothing at all.

12 Calvin Harris On The Aftermath Of His Relationship With Taylor Swift

Dated: January 2015 - March 2016

According to GQ, Calvin Harris had a hard time dealing with the aftermath of the relationship playing out in the press.

"It’s very difficult when something I consider so personal plays out very publicly," Harris explained. "The aftermath of the relationship was way more heavily publicized than the relationship itself. When we were together, we were very careful for it not to be a media circus. She respected my feelings in that sense. I’m not good at being a celebrity."

Swift and Harris broke up and the whole world knew about it. But then again, the whole world tried to pry into the intimate details of their romance before they parted ways also, so it should not come to anyone's surprise that this happened.

11 Harry Styles Thinks Taylor Swift Is A Really Good Songwriter

Dated: Late 2012 - Early 2013

Harry Styles has spoken highly of Swift and her songwriting skills, not to mention says he understands why Swift writes the songs she does.

"We always say we write from personal experience and I think everyone does so it would be hypocritical of us to be like ‘Oh, you can’t write songs’ and she’s really good, so they’re really good songs," Styles said. "So I’m lucky in that sense."

Swift wrote a few great songs in dedication to Styles proving that the two were actually amicable the whole way through.

10 Jake Gyllenhaal Felt Scrutinized By The Media In His Relationship With Taylor Swift

Dated: Briefly In 2010

In an interview with The Guardian, Jake Gyllenhaal was asked about his short-lived romance with Swift.

"I think when you’re in a relationship, you are constantly scrutinized, your friends are scrutinized, but…I would love to not talk about my personal life."

Gyllenhaal obviously felt like his personal life was the subject of too much media attention while he was dating the lovely and talented Miss Swift.

9 Harry Styles Tips His Hat To Time Spent With Taylor Swift

Dated: Late 2012 - Early 2013

During his Rolling Stone interview, Styles talked about his relationship with Swift, explaining that while things could look good on paper, it does not mean they always are.

"Certain things don’t work out. There’s a lot of things that can be right, and it’s still wrong. In writing songs about stuff like that, I like tipping a hat to the time together."

He continued, "You’re celebrating the fact it was powerful and made you feel something, rather than ‘this didn’t work out, and that’s bad.’ And if you run into that person, maybe it’s awkward, but you shared something. Meeting someone new, sharing those experiences, it’s the best [thing] ever. So thank you."

There is clearly no bad blood whatsoever between the two.

8 Taylor Lautner Had A Fun Few Months With Taylor Swift

Dated: Fall 2009

Taylor Lautner described his relationship with Swift as a "good time."

"It was a good time. It was a fun few months there," Lautner said. "I don’t know why you guys want to talk about it. That’s what she does. She writes songs. It’s good music. I listen to it."

The two had a cute and special connection that was even documented in the movie Valentine's Day from 2010.

7 Tom Hiddleston Thinks Taylor Swift Is An Amazing Woman

Dated: June 2016 - September 2016

According to GQ, Tom Hiddleston and Swift's relationship was legit and filled with positivity.

"Of course it was real. Taylor is an amazing woman," Hiddleston said. "She’s generous and kind and lovely, and we had the best time. I only know the woman I met. She’s incredible."

Hiddleston spoke highly of Swift which is not uncommon at all. It seems like a lot of her exes still really appreciate who Swift is as a person, even if they did not work out well romantically.

6 Harry Styles Reflection On Paparazzi Taking Photos During A Date With Taylor Swift

Dated: Late 2012 - Early 2013

Styles was asked about the paparazzi shots that were taken of him and Swift on a date in New York City.

"When I see photos from that day, I think: Relationships are hard, at any age," Styles said. "And adding in that you don’t really understand exactly how it works when you’re 18, trying to navigate all that stuff didn’t make it easier. I mean, you’re a little bit awkward, to begin with."

He went on to say, "You’re on a date with someone you really like. It should be that simple, right? It was a learning experience for sure. But at the heart of it — I just wanted it to be a normal date."

They were both far too famous for a normal date to be possible. And given the level of curiosity about Swift and Styles' relationship, they were never going to be left alone by paparazzi.

5 Calvin Harris Felt like All Hell Broke Loose When His Relationship With Taylor Swift Ended

Dated: January 2015 - March 2016

According to GQ, Harris wasn't pleased with himself after expressing some of his heartbroken feelings on Twitter.

"When it ended, all hell broke loose. Now I see that Twitter thing as a result of me succumbing to pressure," Harris explained. "It took me a minute to realize that none of that matters. I’m a positive guy. For both of us, it was the wrong situation. It clearly wasn’t right, so it ended."

Swift expresses herself through lyrics so was it really that bad for him to express himself on Twitter?

4 Joe Jonas Is Still Friends With Taylor Swift

Dated: July 2008 - October 2008

When asked about Swift writing songs about her past loves, Joe Jonas said, “That’s part of being a musician, I guess. You write songs about each other. She’s great. Yeah, we’re friends. In this industry, you meet a lot of people and you stay in touch. Obviously, it’s tough to be friends with people that are always constantly traveling, but yeah, we’re cool.”

Their breakup wasn't great, given the breakup was done via a 27-second voicemail. But they seem to be doing just fine now.

3 Lucas Till Always Saw Taylor Swift As A Friend

Dated: March 2009 - April 2009

According to MTV, Lucas Till and Swift didn't go through a messy split.

"We dated for a little bit. But, there was no friction because we were too nice," Till said. "We just really both liked each other, [but] most relationships work out 'cause you get along and then you don’t, and then you make up and it's passionate, and with us, I really just liked her as a friend. That’s the only reason that didn’t work out."

They were friends before, during, and after their relationship.

2 Matt Healy Thinks Dating Taylor Swift Is "Emasculating"

Dated: Briefly 2014; May 2023 - June 2023

Despite the fact that media outlets claimed that Matt Healy and Swift were a couple, Healy has said that the two were only casual and "having fun" when they briefly dated from May to June 2023 and that dating Swift would be "emasculating."

"I don’t do anything else, right, so it doesn’t leave a lot of room for me going out, or s***ging someone," Healy said. "So the one time I did have a flirtation with a girl it ends up going everywhere… I mean, I got on E! News and people were like, 'Who’s Matty Healy?' so that was cool."

Healy went on to say, "But I didn’t make a big deal out of it myself. It’s not really anything to talk about, because if she wasn’t Taylor Swift we wouldn’t be talking about her."

"She wasn’t a big impact on my life," Healy claimed. "It’s just interesting to me how interested the world is about Taylor Swift."

Healy also admitted that he felt like if he got into a serious relationship of any kind, be it with Swift or anyone else, he felt like he would be "losing himself in a relationship."

"And the reason I mention that is because if I had gone out with Taylor Swift I would’ve been, 'F**king hell! I am NOT being Taylor Swift’s boyfriend'," Healy stated. "You know, 'F**K. THAT.'

"That’s also a man thing, a de-masculinating, emasculating thing."

For someone who was just having fun with Swift both briefly in 2014 and again in 2023, that is quite an explanation to the seriousness, (or lack of it) of their relationship.

1 Joe Alwyn Has Remained Mum About Taylor Swift

Dated: October 2016 - April 2023

Given his dislike of being in the spotlight, it should not come as any surprise that Joe Alwyn has remained tight-lipped when it comes to the media and talking to any outlets about his and Swift's breakup. That does not mean that there have not been reports from "sources" or "insiders." But, there are no direct quotes Alwyn has made since the two split in April 2023, positive or negative about Swift and that is likely how it will remain for the foreseeable future.

Sources: MTV, Rollingstone, GQ