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].

DEAR MIDLIFE BACHELOR:   Out of the blue, the 25-year old daughter of one of my female friends emailed me a photo of herself in her underwear.   What does this mean?  I have a girlfriend who I am very happy with, and have never given anyone the idea that I’m available or anything.  Should I tell my girlfriend about this?  Should I tell my female friend that her daughter did this?  What should I say to the daughter when I see her?  Jared, Age 45, Mountain View, CA

MLB ANSWER:  Jared – first do the most appropriate thing, and give thanks for fate bestowing this situation upon you  ;o)   You are lucky and fortunate – yes!  Okay – now that we are past that, here is my advice.  First of all, do not tell your girlfriend or your female friend about this … because absolutely nothing good can come from you doing that.  Second, I’d suggest that you not over-think this whole thing.  I mean – the 25-year old could have sent you that photo as a joke … to see how you would react, perhaps.  Or she could have done it because she is interested in you.  If she had sent you a full nude photo of herself, then I’d be more inclined to say she has certain things in mind for you … but based on your reaction in terms of how you worded your question to me, my guess is that it was kind of a joke.  I could be wrong though.  In terms of what to say to the 25-year old when you see her, I, personally, would probably say something like, “Thanks for the photo, Honey” followed by a big smile and maybe an air kiss.  Good luck – please report back with what happens next!


DEAR MIDLIFE BACHELOR:   I have an unusual problem.  I am a fairly attractive woman in her mid forties with a boyfriend who doesn’t want sex as often as I do.  I am used to 3 to 4 times per week.  I am lucky if it’s now once or twice.  I realize different people have different appetites but … how many men would pass on a good old fashioned BJ with no strings attached? Should I subsidize by going outside the relationship for it, or just give up on it.  I love this man. There are no medical reasons.  We just have different needs.  anonymous, Age 46, Texas

MLB ANSWER:   First of all, thanks for the photo … you definitely look like hot stuff to me.   And bless your heart for being in the category of women who will put out – at times with no strings attached.  Speaking for all men, we as a gender greatly appreciate this about you. ;o)   The real question you pose is – if you are not getting enough at home, should you consider cheating?  The answer is – that is up to you, but here are some things to think about.

First of all, would you care if he cheated on you?  If the answer is “no”, then your relationship is probably more of a “relationship of convenience” versus one of true love.  What I’m suggesting is that you are likely overdue for a breakup … and I say that only because fidelity appears to be unimportant at least to you.   If instead you WOULD CARE if he cheated on you, then you have to decide if deceiving the person you obviously love is going to make you feel good about yourself in the long run.  I mean – cheating yields bad karma, and I’m one of those people who think that bad karma follows you, and eventually catches up to you one way or another.  [I’ve had a fair amount of bad karma come back and bite me in the ass – so I speak from experience.]

I’ll take a step back and now say something totally different.  I have known people who could sleep with or cheat on pretty much anyone at any time – and still believe in their heart that they love their wife/girlfriend.  Sex is more like a cup of coffee to this type of person – they can have it or not … with anyone … or not … and they always seem to maintain their overall sense of moral composure.

In your heart, you know the correct answer to your question about whether you should subsidize your relationship on the side.  If it were me, I would carefully consider whether I want my current relationship to work in the long run, and use that to help me decide.   There is a good write up of the various issues surrounding whether or not to cheat in the Short Midlife Articles section – the article is called Is Cheating on Your Wife or Girlfriend Really Worth It?  You might also consider throwing this question out to the group here on our new Midlife Forums. Good luck – please let us know what you decide to do, and how it works out.

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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.