(Jon Wertheim is on vacation this week but we have an esteemed fill-in on the mailbag: Monica Seles. If you think she's thoughtful and candid in this space, you'll want to check out her new book, Getting A Grip.)

Of all your wins, which one meant the most to you? And conversely, which loss was the toughest to swallow? -- Tom Quicksell, Philadelphia

The win that meant the most to me was the first Grand Slam, in 1990 at the French Open. Until that match [against Steffi Graf], I knew I had the possibility of maybe winning a Grand Slam but I never expected to win at such a young age [16]. The most difficult loss was the 1992 Wimbledon final [against Graf]. That was the only time I got to the finals of Wimbledon. And even though I never played my best tennis on grass, I very much enjoyed playing there despite the loss.

What do you consider to be your greatest wins? I vote for your 1990 defeat of Martina Navratilova in Rome, 6-1, 6-1, and your 1993 defeat of Steffi Graf in Australia. With the level of your game in 1991, '92 and early '93, did you feel invincible? -- Omar Gonzalez, West Covina, Calif.

I did play some of my best tennis when I beat Martina in Rome and Steffi in the 1993 Australian Open final. When I look back at the level of tennis I was playing in the early '90s, sometimes it amazes even me!

Serena Williams, after winning the Australian Open in 2007, said she holds you in extremely high regard. What do you feel about the Williams sisters and their mentality on the court? Over their careers, they seem to attack tennis balls with a similar kind of ferocity and mental toughness that you showed when you played on the tour. (Thank you!) -- Andrew Miller, Cambridge, Mass.

Since I retired, I very much enjoy watching Serena Williams play. While I was playing, she was one of the toughest players I ever faced. Her ground strokes are so solid, her serve is one of the most powerful in women's tennis, and mentally she is just so strong. As you will read in my book, I played her when she was 16. When I lost to her, I had the feeling that the new generation was coming and she is going to be one of the best of it.

As a fellow two-hands-off-both-sides player who has been so influenced and inspired by your career, I would like to know if you have any plans to coach? Perhaps through the Monica Seles Tennis Academy? What are your plans post-Hall of Fame induction? -- Ron G., New York, N.Y.

I am very happy that I have inspired another two-hander on both sides! As you know, playing two hands on both sides allows you to create some incredible angles that definitely paid off during my tennis career! At the moment, I have no plans to open a tennis academy, but I am very excited about my Hall of Fame induction. It is a great honor for me.

When looking back at your milestone matches, where do you place your five-set victory over Gabriela Sabatini in the 1990 Virginia Slims Championships final? -- Stephen Males, Bermuda

That was the only five-set match I ever played in my career and I remember that I loved it. Playing Gabi always brought out the best in my game.

Do you watch tennis on TV just for fun? Which players do you like to watch? -- Bobby, Chicago

Yes, I do. I very much enjoy watching Serena, Venus Williams, Jelena Jankovic, Ana Ivanovic and Amelie Mauresmo. I also enjoy watching men's tennis. Like everyone (I hope!), I thought last year's Wimbledon final between Rafael Nadal and Roger Federer was the best tennis I have ever seen.

Which match makes you smile the most from pride of winning, smile the most from giving it your all but coming up short, and which match makes you burn wishing you could play it over? -- Mike Moore, Wilton Manors, Fla.

I think the match I look back on with a smile, even though I lost, was my 1998 French Open final, since just two weeks before my dad passed away and I had a lot of emotions going on inside of me. I would like to play my 1992 Wimbledon final versus Steffi Graf again. There was so much media attention over my grunting (I stopped grunting for this match only) instead of my playing and I got caught up in it. If I could play that match over again, I would have kept true to my style and played the way I was used to playing.

What did your father teach you about angles? -- Kathy, Michigan

As I was writing my book, I realized what a unique relationship my father and I had. He always made sure that tennis was fun for me. He taught me by drawing Jerry (from Tom and Jerry) on the tennis ball and I had to be Tom, and in order to catch him I had to hit the ball on the rise, which created those great angles.

SI Apps
We've Got Apps Too
Get expert analysis, unrivaled access, and the award-winning storytelling only SI can provide - from Peter King, Tom Verducci, Lee Jenkins, Seth Davis, and more - delivered straight to you, along with up-to-the-minute news and live scores.