I think it’s great having a bonded pair (I’ve had several at this point). The main things to consider will be housing during the bonding process (which can be as quick as a couple weeks, or as long as several months), and what you will do if they fail to bond (rare but it can happen). Having all these ducks in a row before you start will make things much less stressful because there won’t be so much pressure on everyone. Speed dating is great, and usually does make things easier, but I’ve also had buns that did great on speed dates still take 3 months to bond! Totally worth it in the end though. 😉
Also, for the bonding process, you need to have some neutral space to work with them in, so an area where no bunny has been, and preferably not within sight of their main areas. This can be a bathroom, bathtub, etc., but it’s nice to know what spaces you will use before you start.
Other things that people don’t always consider are that the new bun might have different levels of destructiveness or litter box training.
Since your current bun is very shy and was not with other bunnies from a young age, it might be date him with a bunny that is very friendly and outgoing towards people to help him learn and feel more brave. It is also a plus if you can find a bunny that was with other bunnies (either bonded or with litter mates), as they tend to be better at communicating with other rabbits peacefully.
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The answers provided in this discussion are for general guideline purposes only. The information is not intended to diagnose or treat your pet. Seek the advice of your veterinarian or a qualified behaviorist.