tsd_writer, lisa_schroeder, cyn2write for the Debs -- and ravelda won the tie. Go ahead and send me your top three choices -- I'll work it out from there :) Thanks for playing!
Oh, and the answer, heh, #4:
When I was a teenager, Val’s Day was hard. I seldom had a boyfriend – and I think I only had one during the holiday until I was in college. It might have been the sarcasm or maybe the touch-me-not vibe DH swears I gave off. I had one boy who liked to trade pranks, but I wasn’t as clever as he, and I think he got bored. Sometimes I thought about joining the Chess club – or the Scrabble club (more my speed) to meet guys. But I never did. In college, it was the week after Val’s Day that my soon-to-be-boyfriend and I went on a walk...er, we wandered. He thought it was a walk, but I didn’t really have a destination in mind (other than landing a date). Strange how these things turn out – my cousin Jonathan, who always had more Val’s Day dates than anyone else I knew, is still single today. Game, set...well, you know how it goes!
Fiona is sarcastic, and she and her 'husband' trade pranks. The cover is a Scrabble board; walk...er is obvious, hehe; Jonathan is the name of one of the key characters; and the last one implies 'match', for MATCH MADE IN HIGH SCHOOL.
Good work to Karen, Cyn, and Thusentha, all of whom most of the clues :)