The 40-Something Guide to Getting Over the 1st Heartbreak

Today we have a 20-something question on getting over the first heartbreak, something almost all humanity has experienced and it never gets easier. How do we move on?

A side note: Anyone can submit a question through “Ask Advice” button above. The idea is to provide a variety of answers and perspectives from 40-something women who have experienced similar situations and come out other side knowing what their outcome was and what they learned. What it is: perspective to help you find your best answer. What it is not: telling you what you SHOULD do. Bring on your questions on career, relationships, money, health…whatever you are feeling in flux about in your 20s.

The quick pic:
Relationship length: 2 years
Time since break up: 1 year
Reason for break-up: “He didn’t think he could ever see himself married”.
Heartbreak ache: He’s in love and talking about getting married.
Her problem: Even though she knows he is a jerk, she can’t let go and move on and is afraid of being alone.

Q.  He was my first long-term relationship and I honestly thought we would marry. His family was my second family. Everything was perfect. Then slowly he slipped away from me, partying with his friends all the time, kissing another girl and telling me he couldn’t see himself married.  I tried to make it work but only turned into the girl I hated. We broke up but continued to hookup. I don’t know what was wrong with me.

I found out in January that he’s head over heels in love with a woman and plans on marrying her. He told me it was different because “she changed me”.  Then he said he wanted to see me as happy as he was because I’m such “a great person” and would set me up with one of his friends. Which is just rude and obnoxious.

I am terrified of 1. being along 2. being heartbroken again. On the other hand, I’m on the shy side and afraid of not meeting someone else. I fear that everyone will fall out of love with me and that I’m not good enough (he always made me feel as if I wasn’t smart enough). I don’t know why I can’t get over it but I have nightmares about the rejection. I can’t imagine the day they actually get engaged. It pisses me off because he was so awful to me but I just have this attachment. I don’t want to be that crazy person that acts like she just got broken up with and it’s been 5 years later. Help!

1. How do you get over an awful heartbreak and basically the loss of them and their family?
2. How do you move on when they obviously have and how do you fix the rejection you feel from it?
3. Where do you meet guys when you don’t want to just barhop all the time?

A. It’s not easy but you will get over it. Not a single 40-something woman looks back and sees herself with their first love. Many women would say, it’s not you it’s him. He wasn’t ready and something just wasn’t right.

This woman says this well and has a few ideas to help you fake it until you make it:

“It is excruciating but you’re the winner here …even though it may not feel that way right now. It’s his problem. You’re amazing and the right one wouldn’t do that to you. Take care of yourself, love yourself, enjoy solitude & socializing. Do what you love and you will meet someone you love. But also there’s nothing wrong with taking time to heal.  I also recommend a book called The Truth Heals.” – 40-something, Santa Monica, CA – 40-something, Santa Monica, NY

One 40-something man had a different spin on that…it’s you it’s not him..but in the end he is saying the same thing:

“It’s not him it’s you. He is a jerk but this happened to you to help you learn something about yourself and hopefully not repeat the same pattern again. His getting married or engaged is probably the best thing that could happen to you because it will force you to move on. Try to look at what it tells you about yourself. Not in terms of what you did wrong but what you can learn to save you from being with the wrong guy.”

Here are more specific and oh so insightful answers to the 1,2,3 of moving on:


“That first true love is blinding and crushing when it is over.  I’m not sure you ever give as much of yourself again for a long time; however, you must stop living in the past and take care of making a future. I too was crushed from a first love and my ex-ended up getting married to his sister’s best friend!  It was such a blow to my ego and absolutely devastating.  As painful as it is, you must remember that he is not sitting around thinking about you, he moved on. You can make yourself insane thinking about how perfect it all was and how his family and friends loved you, and it may all be true, but family and friends that come with a boyfriend, leave with a boyfriend for the most part.  It is up to you to create a new life for yourself and move on.” – 40-something, Brooklyn, NY


You move on one day at a time. There’s no need to figure out your whole future today (who you will marry, when you will marry, etc.).  That’s a big job (and the only one who can actually do that job is God).  The good news, if you are not God, you don’t have to take on His job. Take the next right step. There are no guarantees that you won’t ever “feel” rejected again. Love is a risk…but worth taking.” – 40-something, New York, NY


It’s true that “time heals all wounds,” but it doesn’t just happen without you doing your part. What “your part” is varies from person to person. For some it’s jumping back into the dating pool to meet other men and discover that not only are you likable/lovable, but that it’s possible for you to like/love someone else. For others it’s taking classes, travel, reconnecting with girlfriends, etc. I would caution you to not expect to fall in love and get engaged, only to be disappointed if every guy you meet doesn’t work out this way. Have fun in the process. Make sure you’re getting what you want in a person…don’t settle just because you’re afraid no one else will like you. –40-something, Washington, DC

“You WILL get over the heartbreak but it takes time.  Another, better relationship helps a whole lot too, but unfortunately you can’t just snap your fingers for a new boyfriend.  Spend lots of time with your other single friends and just focus on the friendships (both male and female) that you have now.  When you’re not “looking” for a boyfriend, that is when you’ll likely start a new relationship. – 40-something, Larchmont, NY


“The rejection and hurt may stay in your heart forever.  But, that’s okay.  That is how we move on to new, better relationships.  We learn from the ones that didn’t work out and although our heart may never forget the pain, we can and do heal and reach a place of renewed strength where we are open to giving our heart to someone new.  Eventually, you will realize that this guy was not “the one” and you may even feel relief that you didn’t end up together.” – 40-something, Larchmont, NY


“You have to commit to finding something that takes your focus off your feelings of worthlessness and hopelessness, (to be blunt, your self-pity) and decide (yes, I believe it’s a decision you can make) that you don’t want to feel this way any longer. Tap into you and how many great qualities you have. It sounds to me that this is the real problem … you don’t know and value yourself.  In your own words he treated you poorly yet you wanted to stay with him rather than be alone. Your friends love being with you, so you need to learn to love being with you!!  Losing someone who doesn’t treat you well isn’t actually a loss.  It’s a gift that allows you to find someone who will treat you the way you deserve to be treated.  But you have to believe that you deserve to be treated well or no one ever will.” –40-something, Washington, DC


“It is a massive blow to the ego and emotions and really, time does heal the wounds.  While it is difficult to do, you have to make yourself go out with friends, and get out of your house and your head! Once you start having fun in life, you will meet other people, meet new friends and slowly stop thinking about him as much.  Eventually, you will hardly think of it at all and possibly meet someone new.” – 40-something, Brooklyn, NY



“More and more people meet through online dating services.  Just choose a reputable one if you’re going to try that route.  Let friends know you are single!  Go on blind dates or get fixed up with friends of friends.  Be open to meeting new people.  Smile.  You will feel better and stronger simply by smiling.  We’ve all been in your shoes and although you may feel like you’ll never feel better, you will.  I promise.” – 40-something, Larchmont, NY


“Through friends, at the gym, in classes (that guys would be interested in too … don’t take a sewing class or anything like that!), online dating sites, taking singles trips, joining meet-up groups, at coffee shops, parties, etc.  Anywhere.  You just have to be willing to put yourself out there and keep an open mind.  Even meeting new women friends can lead to meeting their male friends. You have to want this for yourself and do it.  Decide you’re moving on and take the steps to do so.” – 40-something, Washington DC

“There are many opportunities to meet guys if you open yourself to the possibility; however I would encourage you to wait a year before seriously getting involved again.  You need to consider the possibility that another person cannot be the sole source of your happiness and find that in yourself.  Once you are a happy person with self-confidence, you will meet people and find happiness outside of yourself.  That said, you can meet people everywhere – on the bus, at work, at a party, in the dentist office, at the grocery, walking your dog etc.  There is nothing like a common event to get 2 strangers talking.  If you are spending all of your energy on the past, there is very little left for the present!  Start spending time on you and soon you will not even think about him.” – Brooklyn, NY


“Volunteer efforts, church, synagogue, yoga retreats, sporting activities — wherever you spend time with your personal interests/passions.” – 40-something, NY, NY


“Any hobby be it surfing, sailing, rock climbing, tennis, skiing, gardening, hiking (Sierra Club), chess or other games. NOT BARS. Bars are the worst place in the world to meet guys. Especially if you want more than a fling.” – 40-something, Santa Monica, CA



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