Hi Tamar,

Is there anyway to be tactful when specifying the type of woman that you’re looking for? How do I tell if they’re looking for love or just a casual dinner because they don’t want to stay home and cook for themselves that night?

A lot of us middle-aged (55+) single men aren’t interested in angry, divorced women who are still looking for Prince Charming to rescue them and then get angry that we prefer to date younger women who are more lovingly appreciative without all the “heavy baggage.”

Please help!

-Frustrated Older Man Looking

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Dear Frustrated Older Man Looking,

Sounds like you needed to vent and I’m glad you got that out. Dating can be difficult at times and it’s healthy to express that frustration to your friends (or me) rather than let it fester as you review profiles and allow the negativity to seep into your dates.

That said, it is somewhat hypocritical of you to call the women your age “angry” because you sound angry yourself. As for the women your age having baggage… well, it’s pretty likely that you have baggage too. Or, as I like to call it, “a story.” There’s no way you get to middle-age status without one! So try to change your mindset about that because you’re not going to attract any women, regardless of your age, if you’re resentful.

To answer your first question, you can make it clear in the areas that ask what you’re looking for that you want someone who is interested in a relationship and not just casual dating. You can usually tell what women are looking for by reading their profiles thoroughly and asking serious questions when you begin a conversation.

A few weeks ago I wrote about telling “your story” and getting rid of the term “baggage.” And now I’m watching one of my guilty pleasures, The Bachelor, where one of the girls is proudly telling “her story.”

Chris and Kelsey from ABC’s The Bachelor

Kelsey is one of 11 women left on the show vying for farmer Chris’ love and attention. She also happens to have become a widow at the sad, young age of 26 when her husband died of heart failure. This is definitely a big part of who she is right now, just 18 months after the fact, but she technically doesn’t know Chris very well yet and, in fact, hadn’t even been on a 1-on-1 date yet. So, she sneaks away from the rest of the girls and goes to Chris’ room and tells him her story… then they embrace… and then they kiss for the first time… just seconds after she finishes discussing how the love of her life collapsed and died on a sidewalk a block from their home. Then she stares into a camera during an “ITM” (In The Moment) interview with Bachelor producers where she says: “Isn’t my story amazing? It’s tragic but amazing. I love my story.”

Nnnnnoooooooot exactly what I was referring to when I said to embrace your past and honor who it has made you today.

It was correct of Kelsey to tell Chris her story, however, how she did it was wrong. She was telling Chris her story to elicit pity from him and to draw him closer to her.

It is disrespectful to use your story for anything other than allowing someone to get to know you better, sharing about your journey, and explaining how it has made you who you are today. It’s also about timing. A first date isn’t the time to share your story; I’ve said it before but clearly it bears repeating. If you haven’t shared your story on a 2nd, 3rd, or even 4th date — and you can feel the date slipping away from you, then keep your story to yourself, it’s not your lifeline. You don’t want to engage a date by sharing your story, especially if it’s not going well.

But, if you’ve been on a few dates and things are going well, and you want to take it to the next level, then it’s time to open up. The only way to get closer and to bond is to let your walls down and share your story.

As I said in Monday’s post, let’s forget about the negative connotation of “baggage” and call it “your story” instead. But, how do you turn it from negative to positive?

You need to get to a place from within where your story becomes that amazing thing called life that has made you who you are. You get there by accepting your past and your current situation, and then embracing it. Then you need to figure out how to spin it so that it adds confidence and character. By spinning it, I don’t mean lying or manipulating the truth, but seeing the silver lining in all of your life experiences — what you learned from them, or who it brought into your life, or how it changed your life for the better.

You cannot change the past, but you can change your attitude about it moving forward. You do not want a date to feel pity for you with a sob story, so get to the point where you realize that you are the amazing person you are today because of your story, and then tell your story as an adventure. It’s called life. You can live it or let it happen to you.

It doesn’t matter if you are labeled a “mature adult” or an “older adult” — because many dating problems remain the same, regardless of age. In some ways it’s easier, but in some ways it’s more difficult.

Instead of having nosy hookup mothers bugging you for grandchildren, you may have nosy hookup children bugging you to find someone to keep you busy so you leave them alone.

Instead of a bad break-up that felt like the end of the world after a mere three months, you may have 30 years worth of memories that only came to an end because your spouse passed away.

Instead of a drama-filled relationship that ends where you’re able to avoid that person at all costs, you may have three children with your ex-spouse whom you will be connected to for all eternity and have to deal with in some capacity on a near daily basis.

Instead of feeling like your life is over because you’re single on your 30^th birthday, you may have instead embraced your independence and yet still hope to find someone to enjoy the rest of your life with.

These comparisons are the differences in your baggage as an adult dating after 40-ish. Everyone has baggage, whether you want to admit it or not. Baggage has a negative connotation, so let’s just call it – “your story.” Everyone has a story. There’s no way you can get through life without making one. What’s yours?

Not everyone has a backstory, but lots of people do. Positive or negative, when to reveal that story after you begin dating someone you really like is a normal worry — especially when you have something important to divulge.

I’ve written previously about being honest and addressing a physical disability from the beginning; and I’ve written about how to discuss a divorce and/or having children in a minimal way in your profile and on a first date; but how about a backstory that isn’t visible? Are you a cancer survivor or do you suffer from depression or were you abused or were you adopted or any other background that made you who you are… but no one would necessarily know unless you told them?

This type of backstory is not one to include in your 100hookup profile, or even to bring up on a first date, but you do need to open up relatively early on. If the story is too much for your date to handle, then let them leave — clearly it’s not the right person for you and that’s why you need to reveal your story sooner rather than later. Unless it’s relevant to a conversation you are having on a first date, then save your confession for your second or third date. This does not mean that you are ashamed of your backstory, just that you want to have prospects get to know you for you, and not your story, particularly if it is a sob story.

Here’s the kind of profile I steer clear of…

“Don’t lie about your height. If you have issues with your mother, I don’t want to hear from you. That means you’ll have issues with me too! Oh, and guys – I’m not your mother. I don’t need a grown kid to baby. I already had a kid.”

I feel like we’ve had our first fight, and we haven’t even met yet. When trying to sell their good side by arguing with you before laying eyes on you, something tells me I don’t want to go near their bad side.

Mutual fun managers should take a page from mutual fund managers: Past performance is no guarantee of future performance. (Okay, premature arguing does guarantee post-mature arguing.) In the case of guys or gals who previously didn’t pass your smell test, don’t think the rest of the guys or gals out there are equally culpable. Maybe we daters should take a page from the airlines and charge fees for excess baggage.

Oh. And I’m five feet eight and a half.