Is She Robbing the Cradle, or Finding True Love?

Dear Relationshipper,

No sane adult woman would date a much younger guy.  Those guys have some kind of mother complex that just means trouble and doom.  They're just after your money.  I would never do it.

Yep, up until a few months ago I said and believed those things.  Now I'm on a different ship and don't know what to do.  I was at a business conference and of course met dozens of people.  It seemed that every time I turned around, there was one fellow who was really smart and funny and talking to him made the conference much more fun.  He managed to sit next to me during every meeting and when breaks/lunch rolled around, he was quick to offer to get me coffee or a soft drink or food.  He was never pushy or obnoxious and didn't mention getting together in the evening, which I appreciated.

At the end of the three-day meeting, he asked if he could call me and if I would meet him for lunch so I said yes because I really liked him.  He called the next day and we arranged to meet for lunch that same day.  We had so much to talk about - it seemed like a 90-minute lunch flew by so we agreed to meet that evening for dinner.  We spent 3 hours at a restaurant and then I tore myself away and went home, alone.

Over the next few days/weeks we saw each other frequently and I found myself getting in deeper and deeper.  I could tell he was younger but I figured he was around 32-33 and I'm 40 so I figured a few years was no big deal.  People always say I look 34-35.  The actual subject of age did not come up at first.  One night over dinner we were just talking and he mentioned the year he graduated from college.  I nearly fainted when I realized he was closer to 26-27.  I asked him pointblank and he said he was 27.  I asked how old he thought I was and he said about 35.  I told him I'm 40 and he shrugged.

It wouldn't be such an issue if this were just a casual fling but we've really developed feelings for each other and that brings so much more into play such as his family and mine.  His mother is only 47!  Both our families live in other states so we haven't met each other yet but his mother is asking us to visit her at Easter.  My folks want me to bring him home to visit them for Memorial Day.  I've tried to break it off twice but he maneuvers his way back, once by using the argument that Mary Tyler Moore and Demi Moore both are older than their husbands and look at their marriages.

Am I being silly to think this could work?  Am I being silly to break it off?  I've lost my ability to rationalize and could use some help.

Cradle-robbing in Chicago

Dear Cradle-robbing,

Deep breaths for you!  They say that “age is just a number”, but that’s easy to say, tough to incorporate into your life.  However, it’s true.  If your boyfriend doesn’t have a problem with your age, why should you have a problem with his – if the two of you get along great?

There is one, and only one thing holding back your ability to make this relationship work, and it’s your attitude toward his age.  There is absolutely no reason the two of you can’t have an awesome relationship.  He’s already 27, which means he’s already well into adulthood, and you’re only 40!

You know what I’m going to say, so I’ll just say it now: if your genders were reversed, there wouldn’t be a problem.  So why should it be a problem for you?  I constantly hear that there are an increasing number of couples wherein the woman is older than the man.  You’re not alone.  Many use the Demi Moore example – and do you think she goes around fretting about whether Ashton Kutcher is too young for her?  I doubt it!

Love and compatibility don’t come easily.  If you’ve fallen in love with a man 13 years your junior, then so be it.  Yes, your families might be taken aback by your age difference…at first.  But after time passes, they will forget about it.  Do you ever notice that when you have a friend who is considerably older or younger than you are, after you’ve been friends for a few years, the age difference just melts away?  The same thing will happen here.  Your loved ones will get over it (if they even have a problem with it at all).  You can use your close age to his mother to your advantage – you’ll may even have a lot in common, and that’s not necessarily a bad thing!

Again, the only thing stopping you is your own reservations.  If you cease to be insecure about the age difference between the two of you, I guarantee that any problems you encounter will have nothing to do with that difference.

I say GO FOR IT!

Love is sometimes inconvenient.  But who would turn it away?

What’s your story?  Email me at


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