James Middleton—recognize the last name—is the mysterious younger brother of Princess Kate, and Pippa Middleton. Did I mention he was handsome? Oh, I guess I didn’t get there yet. This businessman has two incredibly famous older sisters’, so of course we were interested in getting to know him more. Unfortunately, James has opted to stay out of the spotlight for years. He’s a shy guy who is focused on growing his business rather than rubbing elbows with the elite.
This made us even more curious, of course. You know, when something seems forbidden we just can’t help but be drawn to it. That’s the kind of effect that James Middleton has one us. So we thought it might fun to play matchmaker in our dreams and pair up James with pretty much some of the most incredible women in the world. This is not just based on looks—I took into account interests, sense of humor, intelligence, and more.
At the moment James isn’t exactly a bachelor. He is currently dating actress and singer Donna Air…but there have been rumors for the past couple of months that they have split. What do we believe? My imagination says that maybe James will look at this list of awesome women and opt to soothe his broken heart with someone else. James, buckle up and take look!
15 January Jones Can Totally Keep A Secret
January Jones has quite the resume. She is best known for her role as Betty Draper on Mad Men, and more recently her role in the comedy the Last Man on Earth. She can go from serious to seriously funny in the snap of a finger. January has a 6 year-old son, and after all of this time she still hasn’t revealed his father’s identity. James can bet that January can really be trusted with any royal and family secrets…like pregnancies.
January and James’ ex do look a bit a like, so maybe that can help lure the bachelor in. Either way, I think the stud can appreciate an older woman who he can trust. Plus, James would make a great step dad. His sister Kate has young kids that January’s son Xander could have play dates with.
14 Katy Perry Would Totally Understand Working Hard And Playing Hard
Katy Perry is a world-renowned pop star, a super funny, fearless woman, and a self-proclaimed weirdo. However, this is something that James could love. She’s quirky, fun, and puts her relationships first. Remember her brief marriage to Russel Brand? Well, in the end, he had no complaints except for the fact that they spent a lot of time apart.
However, maybe Katy has learned from this to spend more time with loved ones. Even now, Russel has admitted to being open to reconciliation. Katy isn’t feeling it, but she knows all about working hard and playing hard—maybe James could learn a few things from this pop princess. She is sure to keep things fun and exciting with him, while also exploring the world through her global tours. They can definitely have fun, and she knows all about giving him his space.
13 Hilary Duff Knows The Importance Of Family
Hilary Duff is a former Disney star, but she’s never stopped working her butt off to make it to the top. She is now focusing on her acting career and appearing on the awesome TV show Younger. She has young son name Luca with her ex-husband, and knows the importance of family. Despite being divorced, they still are very friendly while co-parenting.
She and James are the same age, so they are at similar places in their lives, and are probably looking for similar things in relationships too. James has been a stepfather figure to his ex’s 14-year-old daughter, so he could definitely have fun being a stepdad to Hilary’s son. They are both very tight with their siblings, so they will always understand that family comes first.
12 Lily Collins Would Be All Class, All Of The Time
Lily Collins is an a-list actress, and owns each and every runway. Perhaps it’s her British-American appeal that makes her wanted. She was born in Surrey, but has spent much of her life in LA. She is the daughter of musician Phil Collins, she knows a lot about growing up in a ‘famous’ family.
James is a Middleton, one of the most followed families in the world, so he will have no problem ignoring the public with Lily on his arm. Lily is not the clubbing type, so James may have to spend late nights doing something else with her. However, she is always attending award shows, and always gives us sass and fashion envy on every runway. She’s 28, which could be a great age for James since she’s not too young, and may want the same things out of life as him.
11 Taylor Swift Could Bring Him Into The Spotlight
Okay, let’s not all jump at this pairing, but Taylor Swift has dated a lot of guys in show business. She knows it’s time for a change. James could bring her down to earth, and her wholesome personality is something that the royal family wouldn’t mind adding to the family. America’s sweetheart with a British heartthrob that has royal ties—it could be a match made in fairytale heaven.
Taylor is always under a watchful eye—especially with the paparazzi. This may rub James the wrong way. However, can you really blame her for being stalked all day? Oh, and James may want to watch out for her heartbreak singles since we all know Taylor isn’t afraid to name names. But they could really get along. She’s 27, but she’s been trying to settle down with the right guy since the start of her career.
10 Beauty And Brains? That's Priyanka Chopra!
Priyanka Chopra broke into the Hollywood scene with her role in Quantico after a successful career in Bollywood. And she’s been stuck there since, and we don’t really mind it, either. She’s beauty and brains in a gorgeous, exotic package. Priyanka has done so much traveling and has been an active advocate for women. Can she do any wrong? Is she even human?
James could definitely benefit from having this starlet on his arm. Plus, have you ever looked into her daydreamy eyes? He could definitely get lost in those. She expresses herself through her trend-setting fashion sense and manages to stay as far away from gossip as possible. She enjoys the occasional party, but she also knows how to get serious about work. I think he'd love that.
9 Emma Watson Would Always Keep Him Inspired
Emma Watson does it all! She’s an incredible actress, a headstrong beauty, and an out spoken feminist. She is kind, smart, and total girl friend material. She’s also a fellow Brit, so, she will fit right in with the family. There has always been a regal light about Emma, and perhaps this is her chance to fulfill it. She could totally stand by Kate Middleton’s side and support women and children to the world as a royal representative.
If her acting resume isn’t enough to sell James, then maybe her fun and drama-free personality will fill in any gaps. Emma is a total girl’s girl, and I’m sure that’s something James and his sisters can appreciate. I guess you could say that Emma is the whole package, how on earth has she managed to stay single for so long?
8 He'll Never Get Bored Of Rachel McAdams
If James is looking for the girl next door, or perhaps a little mean girl and nice girl melded into one incredible woman, then Rachel McAdams is just the girl for him. She’s beautiful on and off screen. This movie star stays off of paparazzi radar, which I’m sure James can appreciate that seeing as he’s prone to staying far away from the cameras.
Plus, thanks to Rachel’s constant work schedule, she is always changing up her look. She will rock a brunette do for a bit, and then go on to have long blonde hair. She is sure to keep him guessing and keep things exciting. Plus, Rachel is a true beauty. She is drama free, and could be a fun addition to the Middleton family.
7 Emma Stone Would Bring Out His Inner Geek
Okay, this may just be the battle of the Emmas. It’s so hard to decide which Emma should end up with James—they’re both so great. Emma Stone is hilarious on and off screen. She can totally hold her own in any situation. She is known for her quirky and sort of geeky characteristics, and we love that about her. She’s starred in various movies from comedies to dramas and has won an Academy Award, BAFTA Award, Golden Globe Award, and three Screen Actors Guild Awards.
Oh, that’s enough? Well, how about the fact that she could probably make him laugh no matter what? They could be in the middle of an argument and she’ll probably just pull out a simple joke and end it there.
6 Giada De Laurentiis Could Make His Cake Baking Dreams Come True
James has often commented on his cake business that he started with a small loan from his uncle. He loves cakes and baking, so it only makes sense that his next girlfriend would love baked goods and food just as much as he did. Perhaps they couldn’t even work together on a few things. That’s where world famous chef Giada DeLaurentiis comes in.
Okay so, Giada is 47, 17-years James’ senior. But he’s already made a point that age is nothing but a number to him. Plus, Giada looks amazing at 47! I had to double check her age to make sure that I had it right. There’s no doubt that the American-Italian chef could easily charm her way into James’ life given the chance.
5 Nasim Pedrad Would Always Make Him Laugh
In case you’ve been M.I.A. for quite some time, you may recognize Nasim Pedrad from her hilarious skits on SNL, or her role on Scream Queens. Don’t guys love silly girls who are also beautiful? Well that’s Nasim for you. Given all of her experience in comedy, she will definitely make James laugh all day long.
Nasim is very work oriented, yes, even in the comedy field. However, she also knows how to have fun. Given James’ preference to stay out of the limelight, he’ll have no issues supporting Nasim on red carpets. And her ability to stay far away from paparazzi is also the perfect draw-in for James. She will be great to take around friends and family, yes even the royals, no matter the occasion.
4 Emilia Clarke Is Adorable AND Talented
The original Khalessi is up for grabs, and she could definitely blend in perfectly with the Middletons. Emilia Clarke seems like the full package, she’s smart, talented, hard working, beautiful, and easy going. Emilia is from London, so she knows her way around the stomping ground. I’m sure James could learn a thing or two from her.
She is only a year older than him, so they are at similar points in their lives, and seem to want the same things at the moment. They are both focused on work—Emilia on her acting, and James on his business. This may be a draw back, considering they could both seem too busy to focus on a relationship, but if work comes first, then they could at least understand coming second to it.
3 Gemma Arterton Would Fit Right In
Gemma Arterton is an English actress, so she and James will have a lot in common. She’s appeared in films such as Hansel & Gretel: Witch Hunters, and Prince of Persia. This beauty is quiet but talented. She stays out of gossip rags by choice and isn’t caught partying away on the front pages of any tabloid.
She goes from wallflower to stunner with ease. Gemma can definitely help keep James serious when it comes to working. Growing up in England, Gemma is sure to be aware of general royal protocols, so she will always be invited back to the palace. One thing to watch out for is her racier roles on screen. Perhaps the Queen wouldn’t approve of those. But James should be proud to be with a serious actress like her.
2 Demi Lovato Would Always Keep It Real
Can James handle a spicy Latina with a very lusted after butt? If so, then he could totally get serious with Demi Lovato. She has been a great influence on her younger fans and believes in embracing her womanhood and curves. Perhaps the queen may not approve, and Demi does post half naked shots on social media a lot. However, she does it to help other women embrace their curves, so why not support a good cause?
Demi is known for being real online and in person. What you see is what you get with her. I think James could really appreciate this as he is in the limelight whether he likes it or not, and he needs a real woman like Demi by his side.
1 His Beloved Donna Air, Of Course...For Now
I do love a good comeback story. Donna Air and James had dated for years, but it was recently reported that they broke up a few months back after taking a “Break” from one another. Could this have anything to do with the fact that Donna is 8-years his senior, and has a 14-year-old daughter? Perhaps, or it could be for a million other reasons.
Either way, you can’t say it’s odd to go back to an ex, especially if your break up has been recent. Exes get back together all the time, and maybe this make up session could stick if it were ever to happen. Plus, this couple has split a few times in the past, only to get back together once again.