Your question was: Match.com how much to join and was it worth it?.
The way to say it is just to come right out and say it: "have you ever been tested?" If the answer is yes, then "when was the last time you were tested?". Then...the crucial question "When was the last time you were intimate with someone and that does mean even kissing?" It doesnt matter if they were tested 2 years ago ... if they slept with someone 5 months ago...know what I mean?..
This is such a hard question isn't it!?! Sounds like your new back into the dating (online dating with Match.com) game like me. It was hard for me to ask this as well. After my now ex husband cheated on me and I had to go through testing for std's, I didn't want to go through that again. Snafu is right that you just have to come right out and ask. I'd just be sure it's not in the beginning of "something". If he says no will you be able to stop?.
I hate to make you even more nervous, but you probably want to clarify exactly what he has been tested for. Unfortunately, I learned the hard way that a 'standard' course of STD testing does not always test for herpes, and up to 90% of people who have herpes don't even know it because they don't have any symptoms. However, they can still pass it on to a partner. So, you may want to actually suggest that you both go get tested for everything, instead of asking when the last time he was tested. Just an idea.....
It's simple really. Start with "I'm very attracted to you and I know you're attracted to me, BUT I want to be sure that we're both healthy. Let's get tested for every STD in the book and HIV/AIDS BEFORE we take that big step". As soon as we have the results, mine and yours, then we can jump into bed! That should do it...
You need to bring this up BEFORE you get physical. Say it feels awkward for you to ask but it's been so long since you dated and you know times have changed and diseases are out there so you think it's important to have a discussion about safe sex, if he gets tested, etc. Say it's not that you think badly of him but you know this is important and you're happy to answer his questions as well..