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Why You Should Date a Man With Baggage


When you find out a guy has been married before, do you hit the brakes? Worry that he may have too much…baggage? I tell you what: You should be far more afraid of the dudes with zero baggage. I personally have never trusted someone who travels a little too light.

You want a real grown-up man? Date a divorced guy. They know two things: What it’s like to love and what it’s like to lose. Two very critical lessons. And if he has kids? Great. Even better. He has learned that there is something more important than him. He knows what it is to be humbled by love, and to put other people first.

One of the most serious boyfriends of my adult life was divorced, or divorcing (he’d been separated a year). I hadn’t dated anyone in that situation prior, and I found it refreshing to date a grown man with commitments and obligations.

When you date a much younger man (which I have many times), you realize what’s missing–they’re all hope, no miles. But when I started dating this divorced man in his late 30s, I thought he was sexy and sturdy in ways that younger men simply weren’t. He knew what it was to make decisions, and have them blow up in his face. He learned how despite your best efforts, things sometimes fall apart in your hands and break your heart. His biggest disappointment wasn’t, say, that he didn’t get into his first-choice school.

I’m not saying that divorced men are better than single men–but I’m saying that if you write off a dude because he loved someone before, you’re being shortsighted. Perhaps very. This weird idea that we have to be someone’s first love, that he or she can’t have had any life before us, is naive and crazy and, I’ll say it, selfish. Someone’s ex, or exes, their kids, all of it–is not just baggage they carry around–it’s called life. And I want a man with a little on him. Don’t you?

In the end, this man and I were not a match; we ended up wanting different things. When he was fresh off his divorce he warned that he wasn’t about to get back in that situation again. I was like, No problem. Yet as it turns out, he was the one who eventually wanted that coupled, married life back–and I couldn’t blame him. I knew he needed that, but I also knew it wasn’t me.

But it had zero to do with the fact that he had been married before. Not one iota.

I say this because looking for partners or lovers or any rich and rewarding connection is NOT like picking out a shirt. You’re not looking for the one that looks like it hasn’t ever been touched. In fact, quite the opposite.

And by the way, you don’t have to have been married to have baggage. There’s not one person you could meet right now who hasn’t been hurt before. Who hasn’t been let down, left to cry his or her eyes out. Or had to make the tough decision to leave. These decisions are what give us character. It’s how we learn anything worth knowing.

As someone who hasn’t been married or been in a decades-long relationship, I worry about the opposite judgment–that someone will think I’m not capable of sustainable love or long-term connection. And people have as much as told me that. One woman who didn’t even know me said, “Oh, you’re single–you mean divorced?” No, I mean single. “What? What’s wrong? What happened to you?” I know that nothing’s wrong with me–but you can see by her knee-jerk reaction that she, and many like her, aren’t so sure.

(As an aside, I do think there’s something more than a little messed up when it’s more acceptable in our culture to essentially make a very big promise and break it, than to decide not to take it on.)

If we’re going to look at the upside of divorce, it’s that thousands of men and women are released back into the dating pool every day–many of them with a far more open-minded and enthusiastic approach to meeting new people than some of the hardened singles you encounter. It’s true. You want to feel like hot stuff? Date a man who’s fresh out of a sex-free 10-year marriage. Trust me on this one.

So don’t get scared off by baggage. Embrace it. I’d be far more leery of the person who’s got nothing–no carry-on luggage, no past, no prior commitments, no lessons learned, just a toothbrush, a change of clothes, arms swinging  free. Not only is this a near impossible find, but I’m not so sure you’d want him if you found him.

20 replies
  1. JMarie
    JMarie says:

    The marriage stigma is present for women as well. I cringed at the thought of having to tell men I was dating that I was divorced. Not because I was ashamed, but because I knew that there is a stigma attached and very often it turns the man off. It’s like you are used goods, or that you’ve failed. That there is something wrong with you. Or the thought that there was another guy before them. I ended up telling my wonderful amazing boyfriend about 4-5 weeks into dating. We were spending every day/night together and I knew that I had to be upfront. I was scared. I cried. He thought about it for a few minutes then told me he was okay with it. He was shocked and it did take about a day for him to get over the shock, but he was fine with it and we don’t speak of it. One thing he agreed on was that because I had been married and divorced I was much more ready to be with him in a healthy way. I had learned lessons, learned what didn’t work and WHY it didn’t. The things I learned about myself prepared me to be a better person in my next relationship because I knew myself better and I knew what it took for a serious relationship to crumble. We are better off for it and I wouldn’t trade my experience for the world. I HATE it when people automatically discredit men or women because they are divorced. They are missing out.

    Reply
    • Terri
      Terri says:

      I hear ya loud and clear. I’m surprised you waited that long to tell this amazing man, but I can tell it meant a lot to you and you were afraid of ruining it, or changing what he thought of you. I wish I could have been there with you to let you know that someone who loves you, really wants to know you, isn’t going to let you go because you were married once. I bet it was a shock BECAUSE you dropped it on him a month later. I don’t think anyone should be ashamed of being divorced, or labeled because of it. Seems silly–there are so many people going thru it! It’s not anything to be embarrassed about. And I’m glad this guy handled it with grace.

      Reply
  2. Matt
    Matt says:

    I think (hope?) most men get over the idea that divorcee = negative once they reach their late 20s and early 30s. When I was in my early 20s I dated a divorcee with a kid and couldn’t handle it. Handful of years later I dated a recent college grad in her early 20s and it was a train wreck. I know I shouldn’t generalize like this but I have a feeling the next girl I’m serious about is a divorcee because, and again – generalizing -, they just seem to have their shit together. It works works both ways; I can’t imagine the divorcee with a kid I dated when I was 23 thought I was remotely worthy of any kind of long term consideration.

    Reply
  3. terri
    terri says:

    Statistically it IS quite possible that your next love is divorced, and you said, chances are she’s learned some lessons and has her shit together (though of course this is not a foregone conclusion). When that divorcee was dating you, a young 23 something, well, who knows what she thought? But I bet you were balm to her wounds, and a lovely chapter in her life. Don’t put yourself down here. YOu may have helped her thru a very rough time, and reminded her of how lovely and loved she could be. Bravo.

    Reply
  4. Matt
    Matt says:

    I think I might have had some kind of effect; I broke it off after seven months and a week later she met the guy she ended up marrying. Happy for the girl.

    BTW, love the site. Got here via your great piece republished in Jezebel last week.

    Reply
  5. davelynn
    davelynn says:

    Hey, I know this is an old article. But any thoughts?
    what if the guy is divorced twice? the first marriage ended because he cheated on the wife and did something stupid and criminal and got caught.
    The second marriage ended because of the girl.
    Comes out of first marriage with one biological son.
    Comes out of the second marriage with one stepson.

    This is too much baggage right?

    Reply
    • terri
      terri says:

      I don’t know if I can make it any more clear, actually: The rules about baggage only apply if that PERSON poses a problem. Some people can have far more share of “baggage” in their lives, but be just amazing people and you love them regardless of what shit they’ve been through. And then you could date someone who had one bad breakup and he or she never quite recovers. I don’t care why which marriage ended or why. Or what kids he has out of it. I don’t judge baggage by quantity or children or anything else. There’s only one question that matters: Do you like the guy, do you love him. Do you want him in your life. When you know that, that’s all you need to know. Is there a guarantee that you’ll be different, that your relationship won’t end? Nope. No promises in love, period. But if he’s a criminal, and you’re worried he’ll pull that shit again, then you have reason to worry. In my book it’s not how much baggage you have, but how you carry it that counts.

      Reply
    • SassyK
      SassyK says:

      Davelynn I know this is old so u may not be on here anymore. The details dont equal too much baggage, in my opinion. The decision, for me, comes down to his demeanor character lifestyle and behaviors as he is TODAY. None of his past or present circumstances should be excused to the point of your needs as a woman going neglected. You must still be able to obtain respect honor and reasonable contributions from this man that enhances your life.
      Ll

      Reply
  6. Gemma
    Gemma says:

    Having recently been dumped by a man with baggage, all I can say is avoid.
    The baggage this guy had meant his head was all over the place. He was depressed, stressed about all aspects of his life and lived with a mother that couldn’t let go. She wrapped him in cotton wool and wouldn’t let him do anything for himself. Pathetic.

    He didn’t have the ‘headspace’ for our relationship…although he never made any effort throughout the whole thing. I gave him 110% of my heart and got nothing in return. If they have baggaed….AVOID!!!!!

    Reply
  7. Beast
    Beast says:

    Divorce is the public acknowledgment of personal failure. The overwhelming number of divorced people I have known always blame the other partner. It was never their fault. They just picked the wrong person. I say bullshit.
    People who are divorced have proven that they can’t keep a commitment. That they cannot work out differences and that they are quitters. It’s all so very American.
    Terri I think you have some good advice but this is not one one of those columns. Divorced people bring the naivete of the first engagement and the baggage of the failed marriage. There is a whole moving van of baggage there. When you get romantically involved with a divorced person there are three people present. You, him and the ex-wife. Divorcing is not like unbolting two parts; it’s more like sawing apart something that has been welded together. The disassembled don’t just go away intact. There are a lot of jagged edges left.

    Reply
    • terri
      terri says:

      Well, as you can imagine, I disagree w/ you there. And if you don’t mind my saying, I sense the strong tang of resentment in there. Saying all divorced people have failed is as bad as saying all of ANY kind of ppl have failed. I don’t think it’s fair to assume anything of “all” divorced people, and the fact that you do, with such anger/resentment, makes me think you have some painful personal experience here that causes you to lash out.

      There’s ALWAYS other people “in the room.” We all come with past loves–whether we married them or not. The idea that you need to be the first/only is what’s naive. Sounds like you’re scared or have been hurt, and for that, I’m sorry.

      Reply
  8. SassyK
    SassyK says:

    Terri oh Terri. Im sitting in McDonald’s and am so fortunate to stumble upon this WAY_Too_Real synopsis of what is really what. I am sending you two high fives two thumbs way high and a big ass Hell Yea.
    How practical, how real, how accurate, how right on! If a person hasnt or isnt living with dealing with and trying to work through life.. how plastic empty and artificial they must be. I just love the character strength and self love your mature self showed when you admitted you weren’t the one for that guy, with full awareness of how people classify SINGLES as something horrible while esteeming DIVORCEES as something worthy and glorious. You absolutely rock.
    I am now going to embrace my guy with rocky life experiences, baggage, instead of trying to find every reason ro stay in my lonely depressed state of being by claiming he just doesn’t have enough to offer me.

    THANK U!

    Reply
    • terri
      terri says:

      What a lovely note! Thank you. And high five right back atcha.

      I’m glad you’re going back to your relationship renewed…but realize that if he doesn’t have enough to offer, he doesn’t have enough, prior marital status notwithstanding. That’s a diff issue. If someone isn’t bringing enough to the table and you’re doubting it, you need to pay serious attention to that. I just don’t want ppl to swear off divorcees just BECAUSE they’re divorced. But whether he’s a fit, different story.

      Reply
  9. Molly
    Molly says:

    Terri – I found you just in time…I’m not a kid, but a woman of a certain age who has just reunited with an old love. We both want to get going on the life that was interrupted long ago. We both have “baggage” but his is more tangible, ie. immediate. I’ve been telling myself all the things you write about here, but was afraid I was just rationalizing. Now I see that I was not. My guy is the man you describe – one with commitments and obligations, sturdy and dependable. I love this man to the moon and he loves me and I’m happy to take the serious baggage he has along with the joy. Thanks so much for your wise words. Now I know what to say to people who ask “Why are you doing this?” and to feel brave in my answer.

    Reply
  10. Christine
    Christine says:

    Hi, I just started seeing a wonderful guy who is now legally separated from his second wife. He has already stated that he doesn’t want to get married for a third time, which sucks some because I have never been married and I would prefer someone open to marriage at least after a few years. I am wondering if this could possible change two to three years down the road? He’s 60 and I am 57 and he’s the first guy I have enjoyed in quite a while. Knowing this information up front has given me pause–also concerned he’s not a great marriage candidate but am taking it slow. We are hitting it off and definitely enjoy each other’s company and I could see us possibly becoming more in a few months.

    Appreciate your thoughts.

    Reply
    • terri
      terri says:

      OK, my dear. Time for some tough questions. First: You know I can’t know whether he’ll change his mind in three years right? I mean, I’m good but I’m not that good. Plus, this isn’t about what he will or won’t do. This isn’t about him. It’s about you. Women spend far, far too much time wondering if a man will change and if not, how to make it happen. And the answer to that is, no one knows, and if you go into a thing hoping it will change later, then you’ve made a grave mistake. Fact is, if he’s been married twice, chances are, he has already lost this battle once before, and maybe he’ll lose it again–but is that what you want your relationship to be about? Getting him to do a thing you know he may not want to do, or worse yet, waiting around and hoping he will?

      But my real question to you is: Why is marriage so important? Especially now? I could see if you were 32 and wanted 3 kids. Look–neither you nor I are spring chicks here. And at this point, you have to weigh the priorities. Do you want to be with a man you enjoy and could love and who could love you, and spend some wonderful years together? Or do you need a ring and a legal document that says so. Fact is, if marriage was that high on the list of Things You Must Do, dare I say, you might have done it already. I know–you’re thinking you want security. And yet something tells me that at this age, you already know nothing in life is secure or sure–including marriage (and especially with him, since he’s been down that road and turned back more than once).

      I beg of you, do not scare this guy off or throw down ultimatums before you’ve gotten to know him, because of some idea you have of what your life should be. My gut tells me you want to get married to check a box (and I realize I could be wrong), to do that thing you’ve never done. Or to be SURE he couldn’t hurt/leave you. But you know that doesn’t mean it can’t happen (ask his first two wives). I just wouldn’t want you to prematurely dampen a relationship b/c of some thing you’re worried about years down the road. Sorry. I think you should give this a chance first. Don’t rush to label, define, or secure. Try loving him first and see where it goes. If he senses you trying to get him to hop right back into the cage he JUST sprung himself from, you risk losing him. Is it worth it?

      Reply
  11. Kimberly D.
    Kimberly D. says:

    Hey Terri,

    Man oh man, I have so many people against me right now for dating this man that makes me the happiest I’ve ever been. He doesn’t have much money but is the hardest working person I know and loves me unconditionally and that’s more than I can ask for. But, he has two kids and is divorced. I personally, have always believed in abstinence, as I still do, and he completely respects me for that. We’ve been together for 9 months and everyone thinks i’m crazy for going for a guy with so much baggage (compared to me) and I basically have none. The way I look at it is that he has experiences that I never had and we can help each other through everything. I was kind of worried, however, that I was just trying to convince myself that everything was okay and not see the big picture but after reading this column it made me feel so much better. My only issue now is the baby mama, probably one of the biggest pains. However, i’m not the type of girl to simply take sides with my boyfriend just because it’s his ex wife. What’s right is right and what’s wrong is wrong. Anyways, I’ve gone all around the subject, I guess I just needed to vent but thank you for this column, it really made me feel a whole lot better. Thanks!

    Reply
    • terri
      terri says:

      Good! Recognize, tho, that baggage or no baggage, some guys are bad news. And a man with no money but good intentions can spell trouble. I like nice guys, too, but I don’t know if I would want one trying to support me if he couldn’t get it together. Now, you love this guy. And you reference ppl “against” you — I beg you to at least see what they’re saying, and don’t just slap love blinders on. It’s been less than a year–and you’re caught in the sway of romantic love. You’re not exactly the most objective view of this relationship 🙂 Baggage or not, you can learn a lot about a man by looking at the choices he has made and continues to make. I wouldn’t jump into anything legal for a while, and if he can hang in there re: your abstinence and you can, then more power to you! So while I’m glad my words helped, it doesn’t mean that this guy is right for you. It just means that having baggage isn’t always a dealbreaker.

      Reply

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  1. […] world. I learned things that I take with me into relationships with single and divorced men alike. (More on why men with baggage are well worth exploring.) I’m continually challenging my own […]

  2. […] world. I learned things that I take with me into relationships with single and divorced men alike. (More on why men with baggage are well worth exploring.) I’m continually challenging my own […]

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