How to Anonymously Pay for Dating Sites

Paying Discretely
1. Create a new email account. If other people have access to your normal email account or there is a chance someone might see the contents of your inbox, they could see the transaction notifications that come with paying for the dating site. Gmail, Yahoo! and Hotmail are viable options.
2. Sign up for a PayPal account. Not all dating sites will have discrete business names that show up when the fees are charged to a person's checking account. By using PayPal for the dating site fees, the charges will not show up on personal bank statements. But keep in mind bank statements will show money was transferred to a PayPal account. To reduce the amount of emails pointing toward these transfers, use the newly created email to sign up for the account.
3. Use the new email and PayPal account when signing up for the dating site. There's no point in trying to anonymously pay for a dating site if their email updates litter a potentially unsecure email inbox.
4. Pay for several months of the dating site access at one time. It's much easier to explain transferring money to PayPal every few months to pay for using the site instead of paying monthly. Another option is to transfer enough money to PayPal to cover several months' worth of fees. The idea is to avoid monthly withdrawals from bank statements. If the same amount of money is transferred to PayPal every month, whoever sees the account statements will know some sort of service is being obtained, likely leading to uncomfortable questions.