Upside: passion; flexible and open to change; health-oriented; focused on personal best; lovers of variety; intellectually stimulating; great conversation; many interests.
Downside: different philosophies about relationship; less is more (Virgo) vs. more is more (Sagittarius); caution and freedom; thriving in a daily groove meets a restless soul.
Virgo and Sagittarius are both very bendy and changeable. They share a quality (mutable) that means they're adaptable. Together, they make a pair that's always evolving -- never a dull moment here.
One sticking point is that Virgo thrives in the rhythm of the familiar. They can be resistant to acting in the moment, which the racy Sagittarians can find maddening.
Spontaneous Sagittarius is met with a pre-planner in Virgo who wants to plan out the deets first. The Archer is one of the most impulsive fire signs, bursting with enthusiasm to stay in motion. Virgo's momentum is in subtle refining, and getting in a productive groove. Much patience will be needed with this difference in temperaments.
Sagittarius is ruled by lucky Jupiter and is often a born optimist. The Archer takes risks because of a general trust in life. Virgo's need to plan the day can seem tedious and crowd out the joy. It can even feel claustrophobic.
Virgo's ruler is Mercury (and more recently Chiron, "the wounded healer.") Virgos have high standards, and want to make well thought out decisions.
The Archer is a charmer -- many a player is cut from the Sadge cloth. When Sadge flashes that winning smile, something might not add up for Virgo. They sense a wildness in Sagittarius that makes them uneasy, especially if they're eager for a settled life.
The steady-natured Virgo grows uneasy around the unpredictable Sadge. Virgo stays cautious, and while dating can fall into the trap of being the 'naysayer,' the one that curbs the Archer's enthusiasm. Sadge can seem reckless, with Virgo sensing the need to be the "brakes" in the relationship. Too long in this contrary role becomes a drag for Virgo too.
Virgo likes to dig into conversation and become entrenched in details. Sagittarius casts a wider and looser net, and has an aversion for the mundane. Both thrive when ideas can be put into real experience. Virgo has the skills and handle on the steps, and Sadge covers the big picture. At its best, it's a partnership in which both are inspired, and feel appreciated, if not always 100% understood. Virgo helps Sadge bring goals down to earth. Sadge shows Virgo that following an inner call often pays off, and that fulfillment is worth taking risks for.
Virgo likes to create order in the day, while Sagittarius prefers to follow the inspirations from moment to moment. Trouble ensues when Sadge starts to plan travel on the fly, since Virgo needs adventures to be thought out in advance.
A Sagittarius in love will want to reassure Virgo of their devotion, and try to allay their insecurities. This pairing brings up the age-old conflict of freedom vs. stability, and a workable balance is needed here. If a commitment is there, differences can be worked out over time.