Hey, I just started trading and did something really stupid, and now I am stuck with 400 shares of something I don't want. I don't want to take a loss outright, and was wondering what some of the pros would do in my situation? This is a pretty long post, so if you don't want to read it all, I've bolded the questions I am hoping to get answered. - - - Here's the situation: Cost Basis: $2.23 per share Current Price: $1.23 per share Strike prices for options are: $2.50, $5.00, and $7.50. Expiration dates are: Dec, Jan, April, July Low Liquidity in both the underlying and options market. - - - Possible Method of Unwinding: I am considering unwinding 200 shares of my stock at a breakeven point/possible gain/slight loss at the risk of holding 100 shares of my stock hostage. This would be great as that would get rid of half of something I don't want. Here are the current strikes and ask prices of the Dec Put. K: 2.50; P: 1.40 K: 5.00; P: 3.90 K: 7.50; P: 6.40 As you can see, the time premium for all the Puts are the same, i.e. $0.13, since the underlying is trading at $1.23. If I were to buy one, which one should I buy? With something as illiquid as this, would the time premium really decrease as expiration nears? In other words, should I buy it now or wait until it nears expiration? My potential strategy is to buy two puts at a total time premium cost of $0.26. And then sell a July call at a strike price of $2.50, which has a bid price of $0.30. This would give me a $0.04 net gain on the time premium. I would end up holding 100 shares hostage to the July call, since I am trading with a cash account. What do you think? Thanks!