Poor Pippa Middleton!  It is tough going for her as the “royal-adjacent” pretty sister to Her Royal Highness, The Duchess of Cambridge.  Although her parents are relatively wealthy, she isn’t a trust fund baby and needs to earn her way in the world.  Pippa also wants to marry for love and raise a happy family.

Even as there are many advantages to being “royal-adjacent”, one of the biggest disadvantages is her need to marry well.  Because her husband and life partner will participate in royal social gatherings, the height of the society in England and the UK, this man must have impeccable manners, reasonable intelligence and significant wealth (since spending time in this circle of friends is expensive).  Given her natural beauty, as well as her health and fitness lifestyle, it goes without saying that her husband will be equally attractive, healthy and fit.

Pippa Middleton Will Be a Good Friend to Prince Harry

As for recent rumors about Prince Harry and Pippa Middleton hooking up, one wonders if Queen Elizabeth will approve two marriages between the Middletons and Wales families.  Since the Royal Family has a history of marrying cousins, this coupling might be too close for comfort for future generations.

At any rate, even though Pippa Middleton and Prince Harry share many common traits and interests (like endurance sports and outdoor adventures), from a Lil' Matchmaker™ perspective, they have no strong romantic attraction to each other.  As importantly, they are unlikely to injure or pose strong opposition to each other – making them ideal brother- and sister-in-laws.

A Good Time With Nico Jackson

After three years together, in October 2015, Pippa Middleton and Nico Jackson took a break from each other.  One reason for their breakup could be that he now works in a job based in Geneva, Switzerland.  Another reason could be that while he himself has acquired some wealth, Nico comes from a middle class family and may want a more private, retiring life when it is time for him to raise his family.

However, a Lil' Matchmaker™ analysis shows that the nature of their native character is dominant and unproductive together.    While they are attractive, fit, healthy, and demonstrate perfect social grace, these qualities may have allowed them to remain fairly happy during their three-year relationship but are unsustainable for the long term.

A Lucky Break For James Matthews

Before Pippa dated Nico, she was briefly involved with James Matthews.  It isn’t clear why they stopped seeing each other four years ago but getting back together is good for both of them.  They form a harmonious and productive relationship – in this case, Pippa can be especially helpful to James.

Given that he is comparatively wealthy, in marrying James Matthews, Pippa Middleton is able to solve two of her most pressing problems – whom to marry and what to do.  As James’ wife, she can establish herself as a socialite focusing on charitable works, launch a side hustle to nurture her business acumen, become a mother and raise affectionate children, etc.

All-in-all, this pair is a great match!  To make their union even better, they should get pick a wonderful day to get married and Feng Shui their home to reduce the potential for conflict and to increase their income and happiness.