There are a lot of different types of play, and many different types of people, each with their own style. When choosing a play partner, it is important to establish clear boundaries to avoid confusion later. If you want to play with someone, but don't know that the only type of play they do is watersports, you may not be able to handle what you've just agreed to. Some basic things that are pretty much common sense would be that you be comfortable with the person, maybe even have some sort of chemistry. If you want to play with someone because they have a good reputation, but you think they're the dumbest person you've ever met, the scene probably isn't going to go very well. You shouldn't play with someone just because they want you to, it is important that you play because you want to. This can vastly affect your perception on that type of play later, as well as how the scene turns out. If you feel that this person won't respect your boundaries or limits, do not play with them.
So, you should ask:
Type of Play. Not everyone plays the same way, and many don't play how you would expect. Even if someone makes candles for play, they may be into heavy flogging. Make sure that the person you want to play with has experience and is willing to do (or try [if you don't mind the risk of mistakes]) the type of play you're interested in.
Experience Level. For some types of play, this isn't as important. Trying a wax scene with someone who hasn't done it before is fairly safe, as long as they have the sense not to light your hair on fire and/or the scene takes place in a supervised area. For types of play that has higher risk, they need to have experience doing it. A suspension done by someone who can't tie their own shoes could end in disaster. A way around this, would be to have a co-top for the scene, someone who does have a lot of experience in that type of play and could teach the other person what to do, and how to handle the situation if something goes wrong.
For References. When deciding whether or not you want to play with someone, the most important thing you can do is ask someone who has played with that person about their experience. If they had fun, find out why. If they didn't like it, ask about that as well. It may be that they didn't like it because the person was playing "too soft" and that may be exactly what you want from a scene. It is also a good idea to see them play with someone else before you agree to play with them. When speaking with their references, also make sure that the other person played safely. If the person has played in an unsafe way, don't play with them unless you can guarantee that it won't happen again. Do they admit to it? Has it happened more than once, or was it a mistake that they've taken steps to correct (such as a faulty technique, rather than something malicious)? Not only do you want to know what others think of their play, you also want to know how well they are known in the local community. If this person has never been to a group event, and you've never met the person you're getting references from, you should step away completely. If they are known by several local group leaders, and are active in the community, they have more reason to play safely.
Where? Will anyone else be there? Can I Bring a Friend to Make Sure I'm safe? If you have to ask the last question, you shouldn't play with them in a private setting. You should know this person well enough that you can trust them not to put you in a bad situation. If you plan on sleeping with this person and you have in the past, then obviously a private setting may be appropriate in that situation. Also, if there is nowhere to play but their house, it's hard to require that they provide a semi-public play space. It can be a little frightening to play for the first time in a public place, but the more people there are around you, the more people can help if something goes wrong, or if you feel that your boundaries have been crossed.
If the scene ends well, you may want to play with this person again. Wait a few days before making this decision. At that point, you can talk about being play partners on long-term/regular basis. This does not mean that you cannot play with other people. You can have as many play partners as you feel comfortable with. If your play partner is uncomfortable with sharing, this may need to be addressed. Some are, and if you are not in a D/s relationship together, it may be better for both of you (and save a lot of drama later) if you don't become play partners. You will want to discuss how often you will play with each other, new things you might like to try, and talk about travel arrangements if the person isn't local.
Most of this information can be used by tops as well with a little change in wording.
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