Ten Reasons You Don’t Want to Date Me

male and female

Every single mother who is dating has stories to tell.

Sure, everyone in the dating world has stories, but the middle aged single mom stories are a brand all their own.

I had drafted a “just for fun” post today about the ten reasons you wouldn’t want to date me, in which I offered up some of my biggest character flaws as a woman on the market and intertwined them with some of the more ridiculous moments I’ve lived the past few months while navigating this uncertain, unchartered territory.  At the last minute, I pulled the post.  It was humorous, but it was humor laced with sarcasm.  And despite some of my less than stellar experiences in this new frontier, some of those less than stellar experiences laced with a darker brand of humor are best kept in my fingers for now, and as secrets between me and my besties, in a not so public forum.

Instead, I thought I’d jot down the ten biggest lessons I’ve learned over the years about relationships.  Not just love relationships, but all relationships.  Because we can all use a refresher, or at least, I can.

1.       Most of the time, we look at relationships the wrong way.

We’re a society that’s wired to look at situations and ask, “What’s in it for me?”    Versus, “What can I bring to this situation?”  I’m not suggesting I’m the exception to this.   I’m just saying I’m aware.  I’ve seen relationships torn apart by this mentality of “taking,” because when we’re in something for the taking, we always want more, and more is never enough. I’m at my best when I’m giving to someone else and expecting nothing in return.  It’s an ideal that I strive for, yet at times, a mighty one to put into practice.

2.       When expectations and reality don’t match, there’s gonna be a problem.

I’ve let people down this year.  I’ve been terrible at returning phone calls. I’ve reneged on certain commitments.  I had to cancel a slew of plans the kids and I had with friends when I was in New Jersey Thanksgiving week in order to meet family obligations, and I pissed a few people off in the process.  In all of these cases, people had expectations of me that I could not meet.  People had written stories in their heads of how they expected me to respond, or how they expected a situation to turn out, and when reality didn’t match the story they had written, hell broke loose.  I’ve been on both ends of this, the person with the expectations, and the person who’s let others down, and here’s what I know.  We have to be really clear with other people about what we want.  When we are anything less than clear, we cannot expect a situation to have the desired outcome.  Furthermore, if we’re clear on what we want, and we keep getting disappointed by the outcome, then it’s time to adjust our expectations or walk away.

3.       Be careful about making assumptions.

Recently, a friend stopped responding to my text messages.   After a few times of this happening, I had decided that something specific I had done offended her.   I was even fairly certain I knew what it was!  As it turns out, she was going through a difficult time and I didn’t know about it.  In the meantime, I had an entire script written as to why she had stopped talking to me.  The lesson?  Assume nothing.  And if you’re that curious?  Ask.

4.       Don’t take it personally.

I’ve been in some situations this year that have hurt a lot.   In those moments, it was important for me to remember that most people, most of the time, don’t hurt others out of vengeance. Most people, most of the time, don’t even realize when their actions are hurting other people.  Many of us aren’t aware enough to ask ourselves how things we say and do will affect others…and of course, others have simply fallen short of the silent expectations that have been set for us as mentioned above.   In the end, it’s usually “not about you.” On a difficult day, this is a good one to hang onto.

5.       It’s OK to walk away.

A few weeks ago, in a post I wrote about a big revelation I had with my father and my relationships with men, I mentioned that we don’t have to burn the bridge, but we don’t have to cross it either.  If there is someone in your life who is causing you pain, and if asking for acceptance and patience and tolerance just isn’t working, it’s OK to walk away.  If it’s not a situation where walking away is possible, then hover at a safe distance, if you can.  I often expect myself to love and accept everyone, exactly where they are at, without exception.  And while this is a wonderful ideal to strive for, I can’t always put it into practice.  That’s when a polite “See you later” comes in handy.

6.       Understanding is key.

People just want to be happy.  They want to feel loved.  They want to feel accepted.  If you look at the behavior of others, even when their behavior is less than desirable, it helps to remember that the behavior of most people is motivated by these underlying desires.

7.       Being understanding  doesn’t mean you can’t put your foot down.

Sometimes, I’m so understanding that I allow people to behave badly, because I understand where that bad behavior comes from.  Slowly I’m beginning to stand up and say,  “Nuh-uh. That’s not gonna fly with me.”  At that point, someone can change the way they treat me, or I may have to decide to leave them on the other side of that bridge.

8.       Things change.

I spent many a night of my young life crying over relationships that didn’t work out, and dealing with the pain of so-and-so walking out of my life forever.   Last year, after the word got out about my divorce, a funny thing happened. Many of those guys who “walked out of my life forever” showed up in my Facebook inbox, telling me how sorry they were for the way they had treated me and telling me that they wouldn’t mind trying again.  Interestingly enough, I wasn’t up to another try with any of these guys, who a decade or so earlier, I would have walked barefoot through the desert to have it work out with them. However, the message for me through this event was that nothing is forever. Things change.  People change. Circumstances change.  I have seen irreparable relationships mend because people were willing, I’ve seen old loves unite, I’ve seen notoriously stubborn people open their minds.  Knowing that things change helps me feel hopeful in situations with people where it’s difficult to have hope. Knowing that things change helps me remember that I can change too.

9.       Things don’t change.

Although people can and do change, sometimes they don’t.  Never, ever, ever stay in an undesirable situation with someone because you’re convinced they will change – or even worse – that you will be the one to change them.

10.   There is only love.

I could have probably narrowed this “list of ten” post to a list of one, this principle being the “one.”  Because underneath our fears and assumptions and our walking away and not walking away and unmet expectations, and frustrations and hurts, there is love.  You don’t have to go out and find it.  It’s just…there.

As far as not wanting to date me?  To some, I may be a great catch.  To others, not so much. I think that kind of thing is relative.  A man I recently met made the comment that we all have our own messes.  If I can live with yours and if you can live with mine, we may be onto something.

Life is always more interesting when it’s a little messy.



Ten Reasons You Don’t Want to Date Me — 67 Comments

  1. I love this list, Ilene. And it’s only fitting that it ends with love. Heck, what is a great catch anyway? My husband and I fit because we get each other and accept each other’s messes. But I could certainly work on most of the items on this list!

    p.s. I’d love to read that original post. Just saying. 🙂
    another jennifer recently posted…Wordless Wednesday: Winter WonderlandMy Profile

    • I agree that it’s important for a couple or for friends to get each other. And that original post? You know some of my stories already. Although I could just pass it to you under our desks or leave a copy in your locker.

  2. You are a great catch! That’s my subjective/objective heart-as-truth sentiment.
    This list is brilliant and in so many of them, I found myself thinking about friendships more often than relationships. That’s just because I’m not in the dating world right now and I haven’t been in ages. I’m totally in the wild world of friendship, though.
    And I love the comment about nothing being forever. People and circumstances do very much change.
    Tamara recently posted…It Got Weird, Didn’t It?My Profile

    • Friendship can be just as much as the wild west as dating relationships. I’ve had my heart broken a few times over lost friends, too. And it’s crazy but yes, things do and can change. We can’t be attached to that sentiment – because I think that’s just a set up for disaster, but sometimes, change comes around and surprises me pretty hard.

    • And you are a great friend too, Michelle! So luck to have you! And yes, #3 can be a killer. If I were to tell you the story that I used as an example and the reality versus my assumptions…well – there was a mighty difference between the 2!

  3. It’s ALL relative! And may I add that what you put into a relationships, reflects who you are. I have always been able to ‘know’ a person, by observing and oftentimes being the recipient of, their actions/deeds/interactions/commitment/dedication/loyalty etc etc etc. It will become clear if it is a good “fit” as we grow to know them through these things… friend, boyfriend, spouse.

    LOVE your list, my friend. You are a wise wise woman. 🙂
    Chris Carter recently posted…My Favorite Christmas Gifts To GiveMy Profile

    • What you say about observing is SO TRUE. Deeds, actions, loyalty, etc. So much of how we interact with EVERYONE these days is online or via text or email – and as much as bloggers love words, words are just words. I don’t think we can prove ourselves as humans/friends/lovers etc. unless we go well beyond our words and take actions to prove ourselves. I have learned to be an observer the past few months. I’m getting there…even though the antenna’s still slightly broken. xo

    • The messes are what makes us who we are! I believe that! Don’t you feel so much more self accepting of the messes after YTT thought? That was life changing for me in that way!

  4. Jersey Girl (soon to be called something else, gotta find a new nickname- I reckon…) You- my love, nailed this list, back when I was dating, only a few years ago, it was a crazy mess… You are a diamond, darlin’, who is totally worth it. Everyone has something in their past & if they say they don’t, I’m calling BS…

    I’d date ya in a hot minute… if I rolled like that (but I don’t & neither do you… :-)) LOL (sorry, had to throw a funny in there) XO! ~A~
    Amber Day Hicks recently posted…Part V- 120605My Profile

    • Forgiveness! Yes! Forgiveness would have to be on this list as well! I am so grateful to receive it and when I can truly give it. I am always so much lighter when I forgive!

  5. This list is appropriate to so many relationships. I found myself thinking of my friendships. I do #3, always assuming I’ve done something wrong and feeling guilty. And I try to teach my kids #6 everyday. Whenever we discuss school or stuff that’s going on with them, we always discuss that people, all people, want to be happy, to be noticed, to be appreciated – and that has nothing to do with you, personally. Wise words!
    Stephanie recently posted…Crazy and I Know It – Twisted Mix Tape #37My Profile

    • #6 really allows us to see people and their motives through a different set of eyes. It doesn’t excuse bad behavior, but I think it helps understand where people are coming from. I think it’s great that you have these discussions with your kids.

  6. I think you’re a great catch! You’re right that we all have our own messes. I also found it really reassuring that I’m not alone in not being interested in people who I’d have once walked through coals for…if we could remember that in the middle of the hurt, we’d be so much easier on ourselves. Good luck with dating – I hope you’re having fun 🙂

    • Kristi – isn’t it amazing how time changes our perspective on those one time be-all end-all relationships? In hindsight, I would not take one of those men back. And dating? It’s fun. Lots and lots of stories – but there have been a few princes among the frogs, for sure.

  7. Great list! And kindness always wins, it’s always the right response.
    And this list really is not just for dating, but for all kinds of relationships. Everybody needs to read it! xox
    Kerstin @ Auer Life recently posted…OneMy Profile

    • Thanks Ashley. I have worked a lot with my oldest this year on some of these. I hope it gives her some insight that I never had when I was a kid..and saves her some pain, too.

  8. The two items having to do with change really spoke to me, and I think failure to realize them contributes to many failed relationships. If a relationship doesn’t change and grow as the people in them do, it will die. Yet trying to force your friend or partner to change never ends well. Sometimes I wonder what kind of man I’d attract if I were single – a much different one than I did twenty years ago, that’s for sure!
    Dana recently posted…Blogging is putting a crimp in my readingMy Profile

    • It’s strange for me now…to see what kind of man wants to hang around – versus 15 years ago which was more or less the last time I dated. I think a lot of the men are the same, but I just am able to weed them out faster! And one of the reasons I can do so is that I know that what I see is what I will always see – they’re not going to change into what I want them to be. But sometimes, just sometimes, we get this amazing surprise and the change happens.

  9. Oh yes my friend you are speaking to me today! I work on #4 and #9 on a daily basis. I went through a really tough break-up with a good friend of mine almost 2 years ago now but I still think about it ALL the time. I know it was the right thing to do, but it’s always a struggle. Thanks for laying out a sort of “manual” for wading thorough some of life’s messier situations!
    Allie recently posted…Life Imitates Sport – Guest Post at My Own BalanceMy Profile

    • I feel for you with the tough friend breakup. I had two of them in the past year actually, and one I took really hard. BUT like you said and like I said, I have to remember #4. Can’t take it personally.

  10. It is a fine line at times between being accepting and empathetic and being taken for a ride. I am not always good at walking the line. It reminds me of the song lyric ” You’ve got to know when to hold them, know when to fold them, know when to walk away”!

    You write so well! Any Man would be so lucky to live with your mess! 🙂
    Jess recently posted…Thursday ThingsMy Profile

    • Jess, that’s so sweet of you! My mess works for me, I suppose! And you are right about being “taken for a ride.” Drawing boundaries can be hard. When are we being understanding and when are we being taken advantage of? Sometimes, there are no easy black and white answers to those questions.

    • We really don’t know what the other person is thinking until we know for sure. Unless I know for sure, I try to to assume – but it’s easier said than done!

  11. Good stuff here. As I sit each week and listen to the many stories of women in relationships, good ones, bad ones, over ones, barely hanging on ones, just getting started ones, and so on… I have come to know that every situation is different but core things are the same. Thanks for sharing some things you’ve learned along the way.
    Laurie recently posted…Christmas and BeyondMy Profile

    • I 100% agree that the core things are the same. I am also learning more and more that I have to look at my self in the context of relationships and see what I’m projecting into them. When we can stop the projecting, we can begin to see what’s really there in front of us.

  12. I love this list. Numbers 3 & 4 are the ones that struck with me the most because that is what I was going through this week and now that I have had the time to step back, I can see clearly now.

    Relationships are not easy, whether or not they are romantic in nature. Thank you for the sage wisdom to put some things into perspective.
    Krystal recently posted…Climbing Mount’nsMy Profile

    • It’s all too easy to make assumptions. And at the least, I think we should all start to make ones that are a happy and positive, right? I think the problem is that most of our assumptions within the context of relationships is negative. And that trips us up every time.

  13. Very insightful and all so true.. It is definitely important in an egocentric society to realize most things are NOT about you. I’m quick to take things personal sometimes so I remind myself and put myself in the other persons’ shoe to understand where that comment or action stemmed from.. and sometimes I just take a few deep breaths because I can be a tad irrational. 🙂 Have a great one and hope things work out with Mr. Messy! -Iva
    AwesomelyOZ recently posted…Happy Holidays to all & to all a Goodnight (Until 2014)My Profile

    • Iva – I think you nailed it about our egocentric society. We are in a culture where everything is about us – or feels like it should be! When we turn that around, that’s when things begin to change.

    • Well….a nice cut of salmon can get pretty expensive. I could see that getting in the way of someone on a tight budget wanting to date you. LMFAO right back at you.

    • That IS a tight rope for sure! And it’s very hard to not worry about hurting someone’s feelings for walking away. I think that’s just part of being a caring human being!

  14. A wonderful post Ilene! What great lessons that I hope to learn early on being a single mom thrown back into the “dating world” it’s scary, intimidating, and exciting all at once. This year has been such a year of growth for me. You spoke of giving yourself in an relationship and that is something I struggled with in many relationships. Thanks for sharing today and just being YOU!!! What a wonderful, brave woman you are! ~Leah~
    Leah Elizabeth Locklear recently posted…My Top Five Favorite Blogs: (They should be yours too!)My Profile

    • Leah, I can’t wait to see what’s in store for you this year. There are so many ups and downs after the end of a marriage, but amazing things waiting for both of us on the other side. Wishing you all good things, my friend. xo

  15. What stands out to me the most in this list is “Things Change.” Because they do. So often we are stubborn and stuck in our ways and it’s impossible to imagine any other outcome but the one we have preconceived… However, there are times when that long-lost romance drifts back in and despite the fact that you wanted to write this person off forever, maybe there’s a wonderful soul in there and someone who wants to make up for previous wrong-doings. This is (mind you) coming from an eternal optimist and a hopeless romantic who would like to see the good in people and the meaning in an action as powerful as that–maybe the timing wasn’t right before, but now it is. Maybe this person was different then, and has learned invaluable lessons now.

    I dunno.

    In any event, Ilene–you are The Awesome and good things are brewing for you.

    Charlotte recently posted…And the award for awkward Phish show couple goes to…My Profile

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