WOMAN OF THE MONTH – JUNE 2010 Alyssa Milano

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Alyssa Milano has been selected as the midlifebachelor.com Woman of the Month for June 2010!

Now I typically do not select mainstream actresses as Woman of the Month here on midlifebachelor.com, but in this case I felt compelled to choose Alyssa Milano because of her recent work on the ABC show, Romantically Challenged … which unfortunately was just canceled in mid-May – JEEZ.  Romantically Challenged was a very entertaining sitcom based on a midlife mom named Rebecca Thomas (played by Alyssa Milano) who had just divorced after having been married “since Bill Clinton was President”.  The show’s overall theme was, of course, the same backdrop behind the midlifebachelor.com website … many of the midlifebachelor.com audience is also recently divorced and also wondering WTF to do with themselves with respect to dating.  Unfortunately, I only got to watch one episode before it was canceled – and I really did enjoy it.  Shame on ABC for chopping the show without properly publicizing it – had I known about it previously, I would have tuned in to every episode.  But such is life on the small screen, I suppose.

Here is a great video clip of Alyssa Milano that alternates between interviews of her, and clips from Romantically Challenged.  You can get a good feel for the strength of the show because it clearly demonstrates the awkwardness of how the main character, Rebecca Thomas, struggles through midlife dating … because she’s never had to date before (since she originally married the first man she slept with).  I love this clip because at the very end, her teenage son shows up during one of her dates.  I won’t spoil the clip – check it out for yourself.  Does it perhaps remind you of some of YOUR OWN EXPERIENCES when first getting back into the dating world???!


Typically at this point, we attempt to analyze our Woman of the Month pick in terms of the Midlifebachelor.com 14 Types of Women.  Which type or types do you suppose Alyssa Milano might be?  Well, she is certainly a Jackpot (see Types of Women – Jackpot) since she is a high income earner.  If you know Alyssa Milano personally and/or would to share something about her – please add a COMMENT to the comment section at the bottom of this page!

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.