Divorced woman with kids dating a bachelor

Read more questions about dating as a single mother: 

Dating as a single mom

Will guys date single moms?

“Dating as a single mother in my 20s.”


Dear Guys,

I met the most wonderful man (over 40 and a bachelor) last August. Prior to our relationship he had been in only one long term relationship (14 months), in which he was engaged for about 3 months before he abruptly ended it and blamed her for not being over her ex-husband. This relationship ended two years prior to our meeting.

Just three dates into our relationship he told me he didn’t feel he could proceed if I was not open to getting married. Having such a strong connection early on, I expressed that I would be open to marriage. In the following months, he has talked about getting engaged, living together, and getting married. To the extent that when he joined a country club recently he told me he was putting me down as his wife. I have met all of his friends, his parents, and his siblings. He does not hide me, and even talked about me and our future plans in his Christmas letter for his friends, family and clients. Although, five months is pretty fast, it has felt nothing more than natural.

Then, three weeks ago, I noted he was still friends with his ex-fiance on Facebook and I asked him to remove her. I had a cheating spouse and although I feel these are my trust issues, I trusted this man beyond the confines of Facebook. He said he would but then two weeks later she was still there and when approached he said he would not remove her as her family were his friends and clients and he did not want to ‘upset the apple cart’ for what he calls a non-issue. In the meantime, he gets upset with me and blames me for not trusting him, then in a turn tells me that my kids disrespect me too much—they are 13 & 17—and he can’t live in that type of household.  And does not feel he wants to enter into any kind of financial contract with me but he still wants us to move forward and not end our relationship.

Now, I am confused. In my many attempts to talk to him, I get put off, told we live too far away (45 min) from each other and he won’t be able to spend as much time with me anymore as his workload has been increasing. So, I am still confused, bewildered, and feel he is pushing me away. However, instead of wanting to talk about all of this, he tells me he loves me and cares for me deeply. But he tells me he is unsure of how to proceed. He then tells me he needs time to think about everything and that he is not in the same place in our relationship as I am and he doesn’t feel he is ready for marriage or co-habitation.  OH… HELLO… he has been the one all along who has been talking of this.

Yes, I am certainly ready to marry him, as up until now I could honestly say I had met the man of my dreams, my soul mate.  Sure, I felt we were ready to continue to move forward but now I am just confused. I am giving him the time and space for him to think about what he wants, told him to take his time to really make the best choice for him.

I am heart broken to say the least, after my divorce three years ago (married 17 years) I thought I would never open my heart up again to this magnitude. I feel lost and helpless.

Should I wait it out?  Does he just have cold feet?  Am I wrong to think that he has kept his ex his friend because he wants to keep a door open to a possible reconcilliation?  What am I missing?

Thanks in advance for your point of view!


Dear Anna,

Thanks for your question. We’re sorry you’re feeling heartbroken. Hopefully we can shed some light on your situation.

Meeting someone in your early twenties is so simple isn’t it? Typically, you meet, you fall in love, you get married, you buy a house, and you have kids. But beginning a relationship in your 40s is a whole different ballgame. Those extra twenty years are full of life experiences. Some people might call this baggage, but we feel that often has a negative connotation associated with it. We like to say people have just matured and seasoned a bit, as the two of you have.

And it’s that seasoning that has thrown this guy off. He’s finally opened his eyes and realized that if he wants to be with you he needs to accept and welcome the entire package, and that’s what he’s struggling with right now. But from our point of view, you seem like an easy person to be with. You’re open to dialogue, you want to understand your partner and you want to work through issues. Those are some of the important ingredients to having a successful marriage/partnership. If he doesn’t see that, or frankly, thinks he’s going to find a “perfect” situation where he doesn’t have to deal with any issues at all, he’s sorely mistaken. He only needs to look at his own situation to realize that no one is a blank slate, and what makes people interesting—and probably why he fell for you—is who they’ve become based on their life experiences.

As far as his ex-wife on Facebook, well, that is a non-issue. Sure, he shouldn’t have told you he was going to remove her when he really didn’t want to, but we don’t see a problem with it. Typically, people who divorce don’t reunite with their ex. And really, there’s no reason he can’t be friends with her, or remain connected with some of their mutual friends. Just because he didn’t want to be in a marriage with her doesn’t mean he should throw away all the other connections he made while he was married to her. And the fact that he has an amicable relationship with his ex also shows he’s not a bitter and angry person, and one to hold grudges. That bodes well for your relationship if it works out.

We can see why you’d be confused by his behavior though—his backpedaling especially—but from a guy’s perspective it’s pretty typical. Here’s what guys do when they meet someone they’re attracted to.

Stage 1. Pursue, pursue. (They just have to be with this woman)

Stage 2. They finally attain what they were pursuing and it’s bliss. (For a while at least.)

Stage 3. They start thinking she might be the one. (Yes, guys do that too) They’re still in the fantasy world.

Stage 4. Reality sets in. They think, “I’ll never be able to have sex with anyone else. Hmm…Do I want to be with her forever? She might be great in bed but I there’s this other thing.” (Fill in the blank for what that ‘other thing’ might be) And finally he’s thinking about the hot “redheaded bartender” and the “girl at the supermarket” and his “c0-worker” etc. The reality stage is a big deal for guys.

Stage 5. Bolt or commit. (This is the fork in the road. Many guys bolt here, and some guys decide to proceed forward, although still scared.)

Getting from Stage 1 to Stage 5 can take two weeks or two years. (Those are random numbers to illustrate a point. Each guy is different.)

You are currently at Stage 5. And you are waiting patiently. Good for you. 

So to answer your questions(Our opinions):

Yes he’s having cold feet.

And yes, you should wait it out. (For a bit.)

No, he’s not looking to get back with his ex.

Yes, at some point you need to talk all of these issues through. He might be the ‘man of your dreams’ but if he refuses to open up and talk about everything, the relationship will probably never transition from the dream world to the real one.

Good luck and hang in there,


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15 Comments on Divorced woman with kids dating a bachelor

  1. Muoi Pigott // April 20, 2012 at 6:30 pm //

    My story is so much less awesome than Molly’s, but to tell it would be long and complicated and sad so I won’t!I will say though that whether we realize it or not, we put our best version of ourselves at the forefront when carrying on an online relationship. For some people the difference is minor…for some it is major. When it’s online (especially text online) you lack the voice and body cues and a lot of times we fill in those “blanks” with what we want. I did that, and ended up getting burned badly. I’ve since found out a lot of half-truths, lies-by-omission, self-aggrandizing behaviors, etc.

  2. I’m a 47 yr old single mom who has been dating a 54 yr old man for the past 8 months. He pursued me from the beginning. He asked me to be his “steady girl” after a few months and told me he was ready for a relationship. We have spent almost every weekend together since then. We spoke on the phone 5-6 times a day. He would wake me in the morning, I would call on my way to work, he would call in the afternoon when he got up (works midnights), call on his way to work and then again when he found out what his evening was going to be like at work. We rarely texted or emailed…he prefers to speak. We have taken several trips and are great traveling companions. He likes my boys (teenagers) and they will all gang up and tease me. We have all kinds of inside jokes and phrases that just the two of us get. We both love sports and enjoy watching together. I love to cook and frequently make his favorite foods. We’ve only had two minor disagreements and both were resolved within minutes with sincere apologies.
    Late in May, my oldest graduated high school. My parents and my brother came over and my boyfriend spent time with them (first time meeting them). Everyone got along great! He could talk to my brother about sports, my dad about traveling and was very sweet to my mother who uses a walker. He helped her bring her food to the table and helped her get seated. I was thrilled that everything seemed to be going along so great. We were even talking about when we would go to the lake this summer.
    Memorial Day we went to a baseball game together, came back and we cooked for all the teenage boys that were at my house and he spent the night. Wednesday he took off work to go to the baseball game with his buddy and then came over to my house and again, spent the night. Saturday I had invited him over for dinner and I cooked one of his favorites. He got there and handed me an article out of a magazine that had to do with the company I work for and made the comment that he does think about me when he’s not with me…finding things to show me and thinking of things he wants to tell me about.
    Normally he brings a bag on Saturdays and then stays the weekend after he gets off work…but he didn’t bring his bag. After dinner, he had to leave for work so I walked him out. On the front porch he pulled me into his arms and I asked was everything okay…had I done something to upset him. He said…no, but we need to talk. UGH..daggers to the heart. Tears filled my eyes and I asked…what? are you breaking up with me. He said no…but said that he was starting to feel obligated when we talked about future things. He tried to explain a little more but had to leave for work…asked could he come back and I said that yes, because I didn’t understand.
    He called me after work and asked did I still want him to come over. I said yes, of course so he came. We sat on my bed and he started telling me that he needs some time to figure out his emotions. That no woman has ever been so good to him…cooking for him, complimenting him, taking care of him. I was sitting there with tears streaming down my face not looking at him…he laid in front of me so I had to look at his face as he talked. He would brush my tears away and kiss my tears away. He would kiss my forehead and the tip of my nose while stroking my leg. He would get up to get me kleenex and water.
    He said he was scared of his emotions and needed time to figure it all out. I asked was there someone else and he said he wasn’t interested in dating anyone else and it wasn’t about that. (when we met he hadn’t dated anyone for about a year and he’s not a player-even friends with his ex-wife. Divorce wasn’t about infidelity-but mine was). He said he needed time to miss me. He held me tight…let me cry…stroking my hair and scratching my back. He stayed for almost 5 hours before he finally left. He told me that he would call me but didn’t know when…might be a day, 3 days, week…he just didn’t know. But he assured me several times that we weren’t breaking up and that I would see him again. When he left…he took my face in his hands, looked me in the eye and said, you will see me again. He kissed me for a few minutes and then left. I haven’t heard a word from him since and it’s been almost a month.
    Most people are telling me that he broke up with me and was just being nice about it. Several people (guy I work with who knows him, older female friend who has dated as an older woman) think that he honestly got scared but that he will be in contact with me..especially since he came back after work knowing I was going to be upset, was so sweet and loving to me, and spent as much time as he did.
    We had not grown distant, we hadn’t had a fight, he hadn’t pulled away. I’ve been looking at all the articles on how to know if he’s going to break up with you and NONE of that applies to us.
    “Ask the Guys”…what is your opinion? What happened? I haven’t contacted him except for one text message last week with just a “?” to which he didn’t respond.
    What do I do? How long do I wait? Did we breakup and I just don’t know it?
    Thanks for any help you can give me!!!

  3. @Robyn…..We’re really sorry you’re going through a tough time. Yes, you had a break up of sorts, but more of an open-ended breakup. Unless this guy’s a great actor and a total phony, we think you’ll see him again. Didn’t he look you right in the eye and say that to you? And unless you’ve read him completely wrong for the last 8 months we assume you believed him. Questions for you: How long has he been divorced? And: Has he had any serious girlfriends since? See the thing is, when a guy gets divorced it’s as if he’s finally free again. That’s not saying that marriage is miserable for a guy, but there are certain “compromises” he willingly makes. (No sex with other women…ever.) (We also know women make compromises too, but that’s for another time.) Once his marriage dissolves and he gets over the pain, it’s as if the world opens up again and he starts to see all the possibilities. He can now go where he wants, pursue what he wants, work on the projects he wants to, and sleep with as many women as he wants. It’s more a matter of having the choice rather than actually doing it. (Some do, some don’t) Our best guess is that you were unexpected. He hadn’t planned on finding someone like you. Or he wasn’t looking to find someone like you. Someone who treated him like gold, cooked for him, took care of him, probably met all his physical expectations too. In a word, “perfect.” The problem is, he’s not sure if he wants “perfect” or he wants “freedom.” You might say the two don’t have to be mutually exclusive, and we would agree with you. But understand where his head’s at. (At least that’s our assumption based on the info you’ve given us.) He’s likely in a good place in his life. Worked through the demons from his marriage—friends with his ex–and feels comfortable with who he is. He’s trying to figure out if adding another person to the mix is really what he wants. And as soon as talk of the “future” started happening, this is when he started taking a hard look at his life, and what he really wants. A month is a short time to figure that out. We suggest, giving him space. If he doesn’t contact you in the next month, it’s likely you’ve broken up. But we think he will. And frankly, he owes you much more of an explanation—and closure if that’s where this is headed—than what he’s given you. But we’d stop the texting for the next few weeks. See what happens. And the fact that he didn’t respond to your text is a loud and clear message. After that it would be okay to send a nice text saying hi, but let him be the initiator for anything more serious. Please keep us posted and let us know how this progresses. And feel free to ask as many follow up questions as you need. Hang in there.

  4. Thanks for answering!!
    He and the ex have been apart for several years now. He has dated some other women but I am his first serious girlfriend since the divorce. He even mentioned something about that when we had our talk.
    And yes…I took care of all his physical expectations and even taught him a few new tricks. There was really no aspect of life in which we weren’t compatible.
    I remember he also said when we had our conversation that he felt I was giving more in the relationship than he was. Not sure why he feels that way or what that means in context with the rest of the conversation. Any ideas??
    I have taken a vow of at least 30 days with no contact and then we will see what happens. If nothing else, I will be that much further down the road of healing.
    Thank you for your positive words! I haven’t been able to figure out where this all went wrong…and no matter how many different ways I look at it, I still am baffled. Thanks for shedding some light on how a guys mind works and that 30 days with no word doesn’t mean the end. I will keep you updated!

  5. @Robyn…..Well, we like your positive attitude. Hopefully he’ll man up and talk to you about what’s really going on for him. Per your question/our best guess: He’s basically saying that you’re giving more than he is ready to give. And although he loved it, he understands where it comes from and that you’re willing to give yourself entirely to him—that’s what people in serious relationships do— and he’s not sure if he’s ready or able to reciprocate. It makes him uncomfortable. Yes, please keep in touch and let us know how you’re doing and if anything progresses. Take care.

  6. Still no word from him…and I have kept true to my word and not contacted him.
    But I have a question…do you think he even thinks about me during this time? Do I even come to mind these days?

  7. @Robyn……Yes, it’s very likely he thinks about you, and wonders how you are. He also probably has second guessed himself a bunch as well. But that doesn’t mean he’s changed his mind. Hang in there. And just see what happens. Time will tell here. We know it’s hard to be patient with matters of the heart. Take care.

  8. So, I made it 30 days with no contact…and still not a word from him. What do I do now? I’m so confused still and I miss him so much. I just have a feeling that it isn’t over. The very thought of dating someone else makes me sick to my stomach.
    But personally I am doing better. I’ve been exercising and have lost weight and am in a much better place emotionally and mentally. I don’t cry every day and I don’t think about him every minute of the day.
    Do I contact him? Is there still a chance that he will contact me and come back? Was he lying to me the whole time?

  9. @Robyn….Honestly, keep doing what you’re doing. Keep focusing on yourself. If he really wanted to be in touch he would be. It’s hard to say if he was lying to you or not. Probably not. But right now there’s not much for you to do. Hang in there and keep in touch. You sound much more positive, which is nice.

  10. Well…guess who called me tonight…
    He apologized how he left things and for not being in touch. Said he meant what he said but the longer he went without calling, the harder it was to make the call. He said all the same things again..that he was scared of the feelings he has for me…that I was better to him than anyone ever had been. He told me tonight that he’d never been with anyone like me…that I was different from all the other women he’d dated. He said his thinking was all screwed up when it came to me. He said he’d missed me and thought about me all the time.
    But, he didn’t mention getting back together. He did ask me was I seeing anyone. But then he said he would like us to be friends.
    He asked all about my children and what was going on with them. He asked about me and my job and my family. We talked for about an hour.
    Okay…what does this all mean?? What do I do now? He left it with telling me that he will be back in touch.

  11. @Robyn……He’s testing to see how he feels. Well, let’s back up. Yes, he genuinely cares for you, but he’s pretty sure it’s a platonic feeling he has. But he’s not completely sure so he’s just trying to see how he feels. Which kind of sucks for you because he’s keeping you on edge, and off balance. We don’t think he’s doing it intentionally but he’s still doing it. Robyn, keep being patient for a little while longer. See what happens in the next few weeks to a month. But if the same stuff keeps happening, then you need to ask yourself if being friends with this guy is really good for you? Because if you want more with him, and are always hoping that might happen, seeing him as friends on a regular basis—or even semi-regular—is not going to be good for your emotional well-being. Thoughts?

  12. Hi Guys…
    Well..he’s been calling. First it was 3 weeks after the 1st call..then a couple more weeks. Now it’s been several calls in the same week..sometimes twice in a day. He’s fun..flirty..complimentary of me. He asks all about my boys..very interested in their lives and what they are doing. He asked me to tell them hi and then said…nevermind, I’m sure they aren’t interested in hearing from me. I told him he was wrong..that they did ask about him. He then told me he feels so stupid for how he did me and how he left things.
    This past Saturday he called me on his way to work…and then again on his way home. Asked would it be okay if he came by to see me and I said ok. It was a little awkward at first…but he hugged me and told me how much he missed me. We talked and laughed and did alot of the stuff we always did together…and then he kissed me…and it just felt right. I ended up asking him over for Thanksgiving dinner…and he seemed eager to accept the invitation. I do feel though that we need to talk about all this before I involve him in my children’s lives again. I need to know what his intentions are…
    What do you think? What should I do now? I’ve been trying to move on myself..dating other guys but so far nothing more than first dates.

  13. @Robyn……..Clearly you need to see this through because this situation is hindering your ability to date other guys, or at least be open to them. Why don’t you see how it goes over Thanksgiving. Or if you see him sooner. But be careful not to jump in the fray right away. He needs to tell you what he really wants and why he’s contacting you. Is it because he truly misses you and wants to be with you, or is it because he’s lonely, or possibly horny? Seriously, you need to understand these things. And definitely do not involve him much with your kids until the two of you are firmly established. We’re still not completely convinced about his intentions. Keep us posted.

  14. @Dear Guys…………I’m 36 and met a guy who is 28. I am a single mom of 2, full-time job, master degree,etc. We met, things went fast. We dated for 3 months. Within the first 2 weeks, he had a get together at his family so they can meet me. We went to church together. He is a fireman, so when he wasn’t at work, he was with me , stayed every night at my house. He had to be around me if he or I wasn’t at work. He text me all day every move he made. Every now and then he would get angry saying that I was dominate or pushing. And the last girl that pushed him, “OWNED” him, controlled him. I gave him a gift for valentines and he was angry saying that I only gave him that to stay during the bad times. He used to ask me if I would get bored with him. He used to say that if we had a breakup, it would be bad. I got the feeling he was scared I didn’t need him and would leave him. I worked full-time, in college to, plus kids and coach and gave him anything left of me. After the relationship he had previous to ours he was living check to check, had to work all overtime at 2 jobs, house note, car and truck notes and stuff he got when he was with her. In his home all he had was a sofer and tv. He would complain about how he couldn’t even buy a bed or have anything to show, with all the working he does. If feels like he was ashamed of the position he was in. He needed roommates to save money etc. Well one day we had our first disagreement and I got up and walked away. He told me that showed him that I would leave him for good. Which That does not show that all. He called my house crying that night and then the next day came and broke up with me. We never cursed each other, cheated, lied, etc. Now it’s been no contact from him. He ignores me. But once a month he responds to my text. Its been 3 months. This last time he actually called me back but we talked about my son, that is not his. But he sounded like he did not want to get off the phone with me but I ended conversation before it got awkward. But his responding is within minutes now. Over these 3 months I have found out that only weeks before meeting me that his girlfriend moved out and the breakup was because she cheated and had a baby that is not his but he thought was & signed birth certificate.

    After we broke up before he started the no contact, the last text I received said ” I am not the person you know, complete opposite. I don’t have time to be that right now” “I rather be miserable for awhile and fix my own life”” How can I make myself happy with I am not happy. I made the mistake of looking for love when my life wasn’t fix. I blame mostly everything on me. There’s a lot I have to do and I need to solve my own problems alone , I put myself in this position alone.Maybe he thought breaking up was the only way for him to handle his problems. Since our breakup he does have a roommate, the guy he was thinking about asking when we was together. He likes to drink alot especially when he has problems. I never seen him violent but he says he gets violently drunk. He knows I don’t like all that drinking, so I think he doesn’t want me to see him drinking.

    The question I have is what is he thinking? Why is he doing no contact or contacting if he doesn’t want me? or does he? Is there a chance of getting him back? I now know that he just was’t ready and was insecure from the past relationship and I’m willing to be there for him. What should or can I do? My girlfriend says, he’s doing what he told me and fixing his life and if he was done or through with me then he wouldn’t even take the time out to communicate. I want to know your opinion on what possibly can be going on or goals he may have on his side and what can I do to possible have him to initiate the contact instead of me. And its been 3 months, I’m afraid the longer it goes that he will move on. My friend says think of how he was with me and if he responding to me that fast on late night when he’s off that if he was occupied he wouldn’t even bother.

    I do still have his work schedule that he gave me plus the vacation plans we made. His house is on my way to work. I can tell you that if he is not at work at the time he is scheduled then he is home. Stuck in that house.

    Thank you


  15. @Anonymous…..Thanks again for your donation. We do appreciate it. To us he sounds like a project, someone who’s got a lot of figuring out to do. Do you really want to be involved with someone you have to “fix?” Or at least support—at least emotionally— while he tries to get his life together? Remember, you already have two kids that are your first priority. Spending emotional time trying to mend someone who’s broken is going to take away from your children. That’s something you need to think about. Honestly, we know you really dig this guy, but our gut tells us that this is not the kind of relationship you need right now. You want someone who is as together as you are. Those guys are out there. Don’t settle. That said, we will answer your question: We don’t think he was ready to jump into another relationship and he figured that out about three months into things, when some of the crazy hormones wore off. Once things became more “real” he bailed. This should tell you his state of mind. So we keep coming back to: Do you really want to try this again, or wait around for him to get his act together?……..Will he come back? It’s possible. He certainly seems like he might still be interested, but it’s hard to say when he might feel ready? Or, will he still want you back when he’s ready, or will he want to start fresh with someone new? The bottom line: You seem like a woman who’s got her self together. You’re self-motivated, hard working, a loving mother, with still something left to give to a relationship. We think you deserve to have someone who’s in the same boat as you. Don’t you?

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