Where is this going? How to figure out your future by investigating his past.

meadowYou’ve been out with him several times.  Seven dates to be exact.  He texts a lot, but hardly calls.  You see him on weekends but not both nights.  He’s good about being consistent, but there have been a few times when he’s dropped off the earth.  You like him, he seems to like you, but the relationship just doesn’t seem to want to take off.  You feel like you are in a constant state of limbo.  Your friends have their theories.  He’s taking things slow. He’s just shy. You are expecting too much! But none of those hypotheses really resonate with you. How long can you really keep going this way?  It’s starting to drive you mad.  Should you get ready to hunker down for a nice long relationship, or renew your Match.com subscription?  What’s it going to be!!

Ever felt this way?  Most women do.  It’s frustrating when you don’t know where you stand.  Some guys are just tough to read.  Their intentions aren’t clear, or you like them so much that you just can’t be objective.  Or maybe he’s saying all the right things, but his action prove the contrary.  In cases like this there is only one solution.  I know I’ve said it before and I will say it again.  The best indicator of the future is in the past.  If you want to know where this is going, you need to find out where he’s been.

My friend Petra had been dating a guy for two months.  She felt like she was on the cusp of getting a serious commitment.  She was seeing the guy twice a week and felt like it was about time to bump it up to three times. Then another month passed without any change in frequency.  She was stumped.  Why didn’t he want to see her more?  Why was he keeping her at bay?  So she decided to dig into his past a bit for answers.

One night, while out at dinner, she inquired about his past relationships.  In a very casual way she asked, “How many serious relationships have you been in?”  To her shock, her date who was thirty-three years old said, “Only one.”  Petra sat there stunned and then asked, “Well, how long did that last?”  She thought, maybe he was with the same girl for ten years and in that case, I know he can commit. But she didn’t get that answer.  The answer she got stunned her further.  “About six months.” He said.  Petra was more than confused.  Nothing made sense.  He was thirty-three years old and only had one relationship lasting six months?  Needless to say, it was a bit abnormal. Knowing this about him was disheartening on one hand, but comforting on the other.  Well, it’s not me, she thought.  Obviously her guy had problems settling down which was his problem, not hers.

Of course her date made his argument.  He’s just never met anyone that made him want to commit.  But when she really dug into his past she realized quickly that time and time again he always put his career aspirations and hunger for power and money before anything else… including his own family.

“His mother died while he was on a ski trip with business associates.  Instead of leaving immediately for the funeral, he stayed through the week as planned and just sent flowers.  I thought that was super cold.”

If that doesn’t tell you what kind of man he is, I don’t know what will.

Sometimes we hear things that are fishy, like not attending the funeral of your own mother, and even though it strikes us as odd, we ignore it.   We think to ourselves, well that doesn’t have anything to do with my relationship with this man.  That is where most women go wrong.  It has everything to do with your relationship. It tells you what kind of person he is.  It tells you about his character.  It tells you what you have to look forward to.

I remember dating a guy many years ago that I thought had some potential.  He was cute, nice and pretty smart.  Then one day I asked him about his past relationships and he told me that his ex girlfriend cheated on him over and over again throughout the two years they were dating.  When I asked him why he didn’t end it he said he believed she would change.  That raised a big red flag in my mind.  This guy didn’t have the confidence to stand up to his cheating girlfriend?  Was he that much of a doormat?  Did he not respect himself enough to find someone that treated him with respect?  After that night I began to see him in a different light. Today, I’m married to someone else! Someone who would never tolerate cheating – from others or from himself.

If you are dating someone, make sure you probe into their past. It will tell you a great deal about their future.  Sure, some people grow up and reform themselves, but you have to ask the right questions to find out if that is the case.  Don’t shrug off stories that make you question him.  Don’t ignore the red flags.  Don’t try to validate why he did something you would normally find unacceptable. This is the best way to find out who someone truly is. Instead of listening to your heart, listen to him.

Are you dating someone now that has you confused?  Do you need help formulating questions of your own and interpreting his answers?  Email me at coach@jessmcccann.com and find out about one-on-one consulting.  

New! As of September 27, 2011 – You can follow me on Twitter @iamJessMcCann

Posted in dating and hooking up, Dating Coach, Dating Tips, Dating Website | Tagged , , , , , , , | 8 Comments

8 Responses to Where is this going? How to figure out your future by investigating his past.

  1. Nicole says:

    This is so true on many levels. I’ve dated several guys that, had I paid attention to the warning signs from the past, I would have realized were all wrong either for me or in general. But, to be fair, it’s not always smart to write someone off immediately based on a few past events. My current boyfriend readily admits he’s wronged some past girlfriends, he cheated once and a couple of times just by being a jerk. But, those relationships were a long time ago and he’s grown up a lot since then. Our relationship is great: he’s open, affectionate, honest, etc. We had a rough patch, but had I immediately assumed it was going to be like the past, I would have missed out on a great man I love dearly.

  2. SAM says:

    I have dated a guy who would always make me feel as if he wanted a serious relationship . Which at some point or another i really think he wanted a serious relationship but I never payed attention to the things he would say . Ok I would always say i never want to have sexual intercourse with someone unless i was married which i stuck with that . He respected that at first . In the beggining of relationship never kissed him but only hugged because i was trying to see where our relationship was going . He asked to be exclusive after 3 dates i agreed but i still kept my boundaries up . Make long story short our realtionship ended horrible after finding he was cheating but never confroted him in the right way . Did he cheat because i was not physically intimate with him or he really was just wanting to have sex with me ?

  3. Todd says:

    I would not read too much into the past. Im in mid 30’s and have never had a relationship last past a year. Why? Because I recognize significant compatibility problems early on. The people with the real issues are the ones who date the same person year after year when EVERYBODY thinks they are a disaster. I will settle down forever when the correct situation presents itself.

  4. Sarah says:

    I disagree with you some of you references to the past. I am a 29 year old woman and have never had a relationship longer than 6 months. I do not think that it is indicative of a fear of commitment, putting work first, or not wanting to be in a relationship. I have always been open to love and just have not found it yet. If someone based my desire for a serious relationship according to this rule, well I’d never find love.

    Jess, I tend to agree with all your advice, but on this one I have to disagree.

  5. Jess McCann says:

    Sarah, Thanks for your comment. Yes, there are always exceptions to every rule and you may very well be that! The point above is simply to ask questions. In this instance the man in question was in fact a power chaser which was why he wasn’t going to commit. I don’t mean to suggest that everyone that has not been in a long relationship is the same way. Just trying to make the point of asking questions when you find something that raises your eyebrows. Thanks again for your comment and reading my blog!

  6. jc says:

    A guy that “texts a lot, but hardly calls. You see him on weekends but not both nights”, is definitely up to something, he could even be married.

    I don’t know if asking direct questions will get a woman anywhere especially when most guys will straight up lie. And furthermore, if a woman likes a man that much she’ll think she’s the one to change his bad ways. It’s even more of a challenge to her.

    Case in point when you said you dated that guy who’s ex constantly cheated on him but he took her back. You found out he was a doormat, no challenge to you, and you immediately dropped him, sorry, but that’s a typical female reaction, even more why a guy will lie.

    @Sarah, 29 and you haven’t been in a relationship longer than 6 months. Somethings up. It’s either you, or them, and somethings telling me its you, and there’s nothing wrong with that, patience will bring the right one along.

    “he always put his career aspirations and hunger for power and money before anything else”
    I don’t think there’s anything wrong with a guy/girl putting their career first. It’s just one part of the balancing act in the relationship circus.

  7. Curious? says:


    I love your blog because it has given me insight about men!!! I do have a question, what if I met a nice guy that I really like but he judges me for my past?

    I made mistakes in my youth, because I had no guidance. It is a important to see how a man’s past relationship will shaped a possible future with him.

    At the same time, I am distress with the thought of a man judging me for my youthful indiscretions. what if he thinks that I am unworthy of a long term relationship because of mistakes I made or how I allowed myself to be disrespected by jerks?

    • jessmccann says:

      Thank you for your comment. I’m so glad you like my blog and hope you will also check out my books for advice too. In regards to your question…
      I think as long as you explain what you have learned from your past and how you strive to be better now, you can be honest with your guy. If he is not the type to understand and judges you for your past, then you may want to reconsider your relationship with him because in the long run, you want a partner that you can talk to and make mistakes with. No one is perfect and you will both inevitably make some mistakes. How he reacts will tell you more about the person he truly is, and that is more important than being fearful of him judging you. I hope this helps!

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