“Should I Beg Him To Come Back (Again)?”


I have been dating a man for three years. Just recently, he broke up with me in an email with no warning. We had lots of ups and downs, but, despite all the relationship red flags along the way, I love him very much.

I met him only a month after my divorce of was final. (I was married twenty-five years). He was and still is my financial planner. Very early on, he talked a lot about selling his house and moving into mine. It meant moving in with his 16-year-old son as well, and I avoided the subject as much as possible because I wasn’t sure I wanted that.

This past Christmas he asked me to marry him. I accepted the ring and said how much I loved him, and the ring was a sign of commitment. He was telling everyone we were engaged. I was telling everyone we were committed to one another.

We went on a cruise together with my college-aged daughter in January. The vacation was great. On our way home after we dropped my daughter off, he asked for the ring back. No warning. No argument. Just raising his voice to give him the ring back. My jaw dropped. Over the next few weeks, I was the one who kept reaching out. Finally, we were back together. Then a few short weeks later, bam. Same thing. This time he did it over a phone call. I started reaching out again and we got back together. Then suddenly once again, with no warning, he sends the fatal email.

I’d like to know if I should make another attempt to start it all over again. As I said, I do love him despite the ups and downs. Here are some other red flags that I’ve chosen to accept: he disrespects his mother; says he doesn’t like that my daughter is a priority over him; has no friends; is cheap; He doesn’t like that I make more money than he does; admits to depression; is not well liked by my family.

I know deep down that I must be a fool, but this is very hard to just walk away from after three years. — Can’t Walk Away

It’s time to move on and process the end of your 25-year marriage if you haven’t already (and I would be surprised if you have since you started dating this guy a month after your divorce was finalized). Jumping into another long-term relationship without giving yourself time to process, grieve, move on, and just enjoy being single, was foolish…and, ultimately, kind of selfish. You weren’t ready for the things your boyfriend wanted — living together, marriage, merging your lives — and who could blame you? You’d just gotten out of that kind of situation in which you’d spent 25 years of your life.

Where you really made a mistake wasn’t so much ignoring/accepting all these “red flags” you mention, it was not communicating and expressing your true feelings to your boyfriend. You point out all of his flaws, but I think accepting an engagement ring from someone you aren’t ready to marry is a pretty big red flag in itself. And “avoiding as much as possible” a discussion about living together is weak and lame, too. If you can’t say to the guy, “You know, I’m not ready for that step,” then you’ve got a problem. And the problem isn’t really the boyfriend (at least, he’s not entirely the problem), despite all his red flags. It’s YOU and your avoidance.

You avoided processing your divorce, you avoided conversations about the state of your relationship with your boyfriend, and you avoided rejecting his marriage proposal. And now you want to avoid being alone, which, really, is what all the other avoidances have been about in the first place. You’re just so afraid of being alone when being alone is the number one thing that will help you get to a place of readiness and openness for a healthy and happy relationship eventually. Until you give yourself that space and time to heal and to get to know who you are again and what you want, you won’t be truly ready for a relationship. Whether you keep begging for this guy back or run after some other guy who gives you the time of day, you will remain unhappy and unsatisfied and feeling like you’re settling in a relationship. Because the relationship will be built on providing a distraction for you — a distraction from the work of healing.

Please give yourself the best gift you can and remain single for a year. Grieve, if you need to grieve, the ending of both your marriage and most recent relationship. Spend time with yourself. Focus on your own needs and desires. Think about what it is you truly want in a partnership and what you aren’t willing to compromise on. In a year, you will be in a much better place to date, and I think you’ll find that, magically, the men you are attracted to and want to pursue don’t have a long list of red flags.

Oh, and in the meantime, find a new financial planner.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. Avatar photo juliecatharine says:

    LW, listen to Wendy. This guy may have a laundry list of issues but accepting an engagement ring after a proposal when you’re not ready to marry is just not cool. You two have different priorities and your communication leaves a lot to be desired. What exactly are you running after by chasing him? He dumped you-twice-very impersonally,. MOA and take the time to figure out what you really need from a relationship.

  2. LW…he doesn’t want you. Why are you begging for the affection of someone who doesn’t want you? I can’t imagine a worse hell than being with someone who’s there because he pities you.

    Wendy’s right. Accept that this is over. And learn how to be on your own. Be there for your daughter. Then, after you’ve gotten your own life to a good place, you can think about adding someone to it.

  3. Avatar photo Cleopatra Jones says:

    I would also say that you should give yourself a month for each year you were married before you enter another relationship. 25 years is loooooong time to be with someone so I personally wouldn’t get into another relationship for at least 1.5 years, if not longer.
    It will take a good six months to feel like you aren’t even in that marriage anymore and another six months to figure out why it didn’t work or why you were unhappy. Then another few months to finally feel independent and happy with the path your life is on. Plus, you will need another few months to process the break up with this last guy.
    If you are able, maybe see a therapist or counselor. If for no other reason than to work through the demise of your marriage.

  4. Avatar photo Crochet.Ninja says:

    #1 get yourself another financial planner, NOW.

    don’t beg him to come back. go find someone that truly wants YOU, and won’t jerk you around.

  5. No you shouldn’t beg him to come back for all the reasons stated in your letter and all the reasons mentioned by everyone so far. You need to start yourself over from the ground up and you can’t do that with anyone else in tow.

  6. You definitely shouldn’t have accepted a proposal when you weren’t ready to get married. And he disrespects his mother, is upset your daughter is a priority, and has no friends? Don’t give him another chance.

  7. findingtheearth says:

    If I had depression, someone would not move forward with me, and then kept “reaching out,” I would want to eventually move on. You are stringing him along without any real discussion on what you want out of the relationship. You need to let go and deal with your issues.

  8. Bittergaymark says:

    By all means YES! Beg him to come back! Especially if you want to appear needy, pathetic, and desperate…

    1. Sunshine Brite says:

      And be sure to give him more of your money and free reign over your financial future. Not.

  9. pebblesntrix says:

    WWS. Also, his increasingly de-personalized ways of re-breaking up with you speaks volumes. Likely they are less a sign of disrespect and more a way to do the thing without being persuaded to change his mind as evidenced by your badgering him after each break up to get back together. He’s really trying to end this but right after breakups most people always have doubts or remember the good times and miss things about their partner so his receptivity to getting back together shouldn’t be seen as his true desire–if so, he wouldn’t keep breaking back up again. Learn to be alone. If he wants to be with you, he’ll come to you but your begging isn’t doing anything because on some level he is not all-in but rather has checked out. Accept that and move on. Besides, as Wendy said, it’ll be better for you in the long run and attract partners with whom you’re much better suited.

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