How to Tell Him the Bad Stuff on Dates (And Should You?)

One of the key differences between dating now versus when you were younger is that now you most likely have some baggage. So, how to tell him the bad stuff when you are dating a new man? The wonderful things are easy to talk about, the not-so-wonderful things can be awkward and scary.

I’m sure you have many challenges you’ve overcome or are still living with.  Your stuff may be about troubled children, financial failures or turbulent past relationships. Whatever it is it you know it may impact someone’s opinion of you.

I often get letters about this. I’ve declared bankruptcy. My 30 year old child has a drug problem. My elderly parents are exhausting me. Often, the writer isn’t even dating because she assumes no man would sign on to her mess. Or simply because she doesn’t know how to talk about it.

My response in a nutshell is always this: If it’s something you can change and improve, get to it. If not, the past is the past and you are who you are.

Learn how to present it in the most positive way possible and then be fair and honest with your date. Also realize that this is part of life! You’re still a magnificent woman. And, lastly, I bet he’s got his own hot mess somewhere too.

Here is an email exchange about this topic. I advise that you also read my article Imperfection Does Not Equal Rejection. (I am also divulging some very personal information here. I figure it’s time for me to do so.)

Dear Bobbi:
Can I ask you a very important question?
I have multiple sclerosis diagnosed in 1992. I have symptoms today…I do walk like I’m drunk sometimes, will walk into not living stationary
Items (like a parked bus) sometimes and sometimes I’m wonderfully
fine. I am mobile, do not use a cane or any other devices, however
after sitting,  (when I get up, like from a date) I become very stiff, which is apparent when I try to go to the bathroom.

When I’m on a date, I get extremely self conscious of my
walking, which kicks off my nervous system, which kicks in my

When is the right time to tell a date that I have MS? I get so much
advice from so many people, but I’m tired of men staring at my walk
when I try to leave from the date and NEVER getting a call back. When
we’re sitting everything is fine. He leans into me, touches my arm,
talks very close, until I get up.

ANY ADVISE? I truly appreciate your help on this. Thank you.

Dear A.
My advice on this is better than you think because I, too, have MS. I’m lucky because my symptoms are very minimal. (Knock wood.) I had the same issue as you but, honestly, I had more time to tell someone since it wasn’t apparent.

My rule was to tell when I thought dating might be turning somewhat steady. (I didn’t have to tell many men because I seldom got to that point, btw.)

The men I did tell were not bothered at all. I was so freaking nervous and when I finally got the nerve to say something they were like “oh…okay. So, what’s for dinner?” That’s about how it happened with Larry. And then he read up on it after our date. (Which I didn’t learn for a couple years.)

In my case I had one more thing going for me: When I was diagnosed and literally couldn’t walk for a week, I had no choice but to accept help from my family and friends. That helped me realize that it was okay to need people. I found the delight and acceptance in not doing everything alone; something I had worn as a badge of honor for most of my life.

Your case a different because you have symptoms. I can understand how that’s a tougher situation. I suppose you really do need to tell them early on. You don’t have to give them details but you also don’t want to leave it to their imagination or have them leave knowing you’re not telling them something they feel they should know.

I recommend having what I call a “prepared statement.” It’s something you have scripted that helps you say what you need to positively and with comfort.

Toward the end of the date if you’re having a good time you might say something like this: “By the way, Bob, I have this neurological thing that affects me occasionally, and it gets a little worse when I’m nervous…like when I’m on a date with a nice man.” And then smile.

Or you can say something like, “My legs get stiff after sitting for so long and it takes me a bit to loosen up. May I hold onto your arm while we walk to the car?” This gives him a chance to step up and be needed, which is something good guys crave.

Most men are quite taken by a woman who can be honest and vulnerable. At minimum he will appreciate your honesty. That doesn’t mean he won’t choose to not see you again.

I have to be honest, and I know you know this: some men won’t deal with it, especially because they don’t even know you and aren’t invested yet. I don’t think that makes them jerks necessarily; this can be a tough thing for someone to understand.

If he wants details just give him the minimum he needs to know at the time and let him know, if it’s appropriate, you’ll share more later. And go straight to the point; no stories…just the minimum facts, ok? And if you, like me, find something positive in it, definitely lead with that.

Remember that this is just one small slice of who you are. Don’t be afraid or ashamed to share it. The key, I believe is to be honest and up front, but to wait a while into the date after he gets to know you. He can then weigh that against other attributes he likes about you.

I hope this helped you get more comfortable telling a man your bad stuff. Just remember, there’s tons more good stuff to go along with it.

I wish you so much good health and love. Keep at this and you will find that good man. He’s out there.

With love and support,


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