People write in to ASK MIDLIFE BACHELOR with questions.  An index of all Q&As is located on the ASK MIDLIFE BACHELOR INDEX page. Email your question in complete confidence to [email protected].


Usually people write in to me (midlife bachelor) with questions – but in this case, I’m asking MYSELF and THE WORLD the question about how Jesse James could possibly cheat on Sandra Bullock … especially given who he cheated with (the woman in the photo – Ms. Michelle Bombshell McGee).

When I think of a typical midlife crisis affair, I think of a man in his 40s who has been married a very long time to someone he has gotten bored with … and because he thinks perhaps that life is passing him by, he goes ahead and samples the merchandise. Sometimes that sampling leads to leaving his wife and his previous life behind for something new and exciting. Sometimes things like that work out best for everyone involved. But I cannot possibly imagine how any of what I just said could ever apply to Jesse James’ marriage to Sandra Bullock. She is one of the hottest actresses in Hollywood … makes a ton of money … loved and trusted Jesse James like no other … and just received her first Academy Award … when BOOM the word about this affair got out.

Maybe this was a crime of opportunity for Jesse James. Maybe he thought he’d hit it, and that would be it … but from everything I read, he apparently had an ongoing affair with this heavily-tattooed woman.


There are reports of many text messages … multiple encounters … all apparently while Sandra Bullock was away filming her latest movie, The Blind Side. Anyone else see the irony of the title of her movie?  Wow.

Anyway – if you read more of this midlifebachelor.com website, you will see that I view cheating on a wife or girlfriend as bad karma … which means that doing bad things will eventually catch up to you, one way or another. Jesse James got busted, and the karma is especially bad because of the appearance of the woman he cheated with.

I opened a discussion about this over in our Midlife Forum, here is the exact thread,

A New LOW Has Been Achieved (Midlife Crisis Affair)

and it was suggested that Sandra Bullock might have some blame for hooking up with Jesse James to begin with … because Jesse James’ second wife, adult film star Janine Lindemulder did prison time for tax evasion – so one could say that it should have been obvious to Sandra that Jesse did not always make good choices. But hey – she probably liked the “bad boy” image of Jesse James … so he could have been Sandra’s “Midlife Crisis” relationship.

So I guess my real QUESTIONS are:

  1. How could Jesse James possibly cheat on Sandra Bullock?
  2. If Jesse James was going to cheat, why would he cheat with someone who is covered in tattoos?
  3. Does any blame for this rest with Sandra Bullock for choosing to marry someone who could be perceived as having displayed poor judgment in the past with respect to relationships?   Did she simply think that his previous bad judgment was an anomaly (versus a character trait)?
  4. Two months ago, it was John Edwards, last month it was Tiger Woods, and now this month is it Jesse James.  Who is next?

MIDLIFE BACHELOR ANSWER:  This is one case where I just don’t have the answers. If you have an answer, then please feel free to opine in the COMMENT SECTION below, or on this thread in our Midlife Forum:

A New LOW Has Been Achieved (Midlife Crisis Affair)

UPDATE – due in part to the volume of email I receive from women whose husbands have cheated on them, and are divorcing them (due to a “midlife crisis affair”), and who seek advice from me, I have added a new article here that gives some good basic advice for situations like this:

How to Deal with a Midlife Crisis Affair and Divorce

There is also section of midlifebachelor.com dedicated to the idea of a Midlife Crisis which could shed some light on Jesse James’ behavior:

Your Midlife Crisis

Plus there are several cheating-related short articles here on midlifebachelor.com:

  1.   Advantages of Cheating on Your Spouse or Girlfriend?
  2.   Is Cheating Worth It?

There are a number of Midlife Crisis Affair-related ASK MIDLIFE BACHELOR questions and answers … which could serve as background information:

Christian Wife Waits Out Husband’s Affair
Blatant Affair with 23 Year Old Married Woman
Best Friend Hitting On My Tramp Wife
Physician Husband Cheats on PhD Wife
Should I Leave My Wife This Time (for having one night stands)?
Husband has Overseas Girlfriend
Over-Estimating a Sex-based Relationship
Husband has his Cake
Long-term Impact of Infidelity
Husband’s Affair w/20 Yr Old OK with Wife
Woman’s Sexual Appetite Outpaces Boyfriend
Wife has Occasional Secret Life
Midlife Love Triangle
Cheating Midlife Husband Update
How to Get Cheating Husband Back from Midlife Crisis Affair?
Cheating Wife Now Destroying Man’s Credit
Should Man Divorce Cheating Wife?

I would like to send my condolences to Sandra Bullock.   Midlifebachelor.com supports you.

Avatar of Greg Smith
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.