If they didnt receive the 1st email, its 99% guaranteed they will NOT receive the 2nd email, reason being is THEIR ISP is either denying your email totally from being delivered or putting it in the users SPAM box/folder.
If you have a dedicated server, you need to view your email log and find out why that users emails arent being delivered, if they are being accepted from your server with a 250 sent msg in the log, then its their ISP thats the issue and its going to their spam box.
If this is a vhosted account, you will need to verify your domain name conforms to the basic RFC rules of email sending, as only your host can view the email logs typically.
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