How to Handle Your Baggage When Dating after 40

If you are dating over 40, 50 or beyond, you ought to learn how to handle your baggage on dates. That nasty divorce, the bankruptcy, your high maintenance child, an STD or some other health problem…these are just some of the common products of a rich and varied, well-lived life.

As The Dating and Relationship Coach for Women over 40, one of the critical dating skills I teach is effective Baggage Handling. That’s right: how you handle your life stories – both internally and with the people you meet –can make the difference between never getting past a first date and finding your heart’s desire.

Premature Baggage Bonding, or PBB, is a first-date trap that I see as the most common mistake made by singles dating in their 40s, 50s and beyond. Men and women do it equally, and falling into the trap is easy.  You don’t even know it happened until you’re saying goodbye to someone you like, knowing there will be no second date!

Sadly, premature baggage bonding kills the potential for countless would-be wonderful relationships.

PBB is when a first or second date shifts into a “deep” conversation after you discover some baggage you have in common. It starts off innocently with a question like “So what happened with your marriage?” And off you go! The talk begins about your horrific ex-spouses. How they were alcoholics, or cheated on you or were bad with money.

Maybe PBB begins when you proudly share your sobriety and start sharing about your history of addiction. Or one of you talks about a health issue, and before you know it you’re comparing the scars of your knee replacement surgeries or trying to one up each other about your horrible your hospital experience.

None of this is sexy. None of this is attractive. None of it creates a positive start to a good relationship.

If you’ve met via online dating you are particularly vulnerable when one of you asks “So how is online dating going for you?”  Or “How long have you been on match.com?”  Sounds innocent enough, right? NOT! It’s the gateway to PBB.

It’s human nature to look for similarities. Sharing common experiences is an easy and tempting way to bond with someone. If you met online it’s a natural starting point for discussion.  But comparing and contrasting your craziest, worst or even best meet date is only a losing proposition.

Handle Your Baggage by Avoiding the Bonding Trap

Resist the temptation to “go there.” If you find the conversation moving in one of these negative directions, notice it and divert! It’s just as easy, and much better, to bond over your positive common experiences.

Once you become aware of the temptation to baggage bond, redirect by using some variation of “Sounds like we have that experience in common. Maybe once we get to know each other better we will share more. For right now I’d love to learn more about your life today. Tell me more about the photography class you are taking.”

Here’s is how I advise my coaching clients to answer the dreaded “so how has online dating been for you so far” question: It’s going fine. I get to meet great guys like you. How is your coffee?  Answer politely, positively and move on.

If you spend time on your early dates bonding over your baggage, 99% of the time you won’t be seeing each other again. After sharing your communal dirty laundry, one or both of you may realize that you learned something that turns you off. He may be embarrassed about sharing too much and be nervous about trying to see you again. Or you may start to associate that person with the less pleasant aspects of your past. It all points to going in a bad direction.

It is your job to keep your date from going down this road. He’s not getting advice from a Dating Coach for Men Over 40. You are, so it’s your responsibility to save him (and you) from the curse of TMI.

I’m not asking you to pretend to be someone you are not.  There is a time and place for revealing yourself, but the first or second date is not the time to lay it all out there. So, if you find yourself PBB-ing, gently but firmly move the conversation to another, more positive, topic.

If you do end up together for the long term, there will be a lifetime to learn all the gory details of his divorce, or your financial problems, or his gout. And by then you will both know how wonderful the other person is despite – or even because of – your baggage.

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