Most Helpful Guy
side as in she has a boyfriend and sleeping with me on the side? tough one 90% no but there is a 10% chance of yes depends how hot and how much of useless her boyfriend is... but if you mean side as in friends with benefits kind of thing then yeah sure why not.
Most Helpful Girl
Never. My moral compass strictly prohibits me from ever wanting to knowingly mess with a person who is already in a relationship. I find it disgusting to help someone cheat. I know that technically I wouldn't be the one breaking any promises or doing any of the actual cheating, but just being the "helper" is immoral enough. Compare it to robbing a bank. The cheater is the one robbing the bank, and the helper is the one sitting in the car outside waiting for them to get out, so that they can drive away together. The helper isn't robbing the bank, but they still have a part in it, and in the eyes of the law they're just as much of a criminal as the person who physically took the money.
If we're talking about a poly-relationship in which the partners are allowed to have "side people" but they still consider each other to be their main, then my answer would still be no. I'm a monogamous person. Sleeping around or not being in a monogamous/committed relationship is not my thing. I can respect their dynamic but I do not wish to be a part of it.