Dear Shantell,

Your site has been immensely helpful to my soul in trying to deal with a recent breakup. I’d be very grateful if you would listen to my breakup story and let me know your thoughts on what happened…

I was dating a girl for 3 months. She’s 37, has a great career and owns her own place and wants to have her own family/kids one day. When we first met she told me she had high walls and knew it was a problem and was working on it. She also let me know that she has not had sex in 2 years. She said her walls were high because she’s been burned from bad relationship in the past. In particular a 5 yr relationship (4 yrs ago) where the guy was emotionally abusive and cheated on her. He even proposed to her but she turned it down because she wanted him to change. She actually went to see a therapist following the end of that relationship. I also learned early on that honest/trust were her deal-breakers. I learned all this in the first couple dates. I was initially dishonest with her about my living situation (I was living at home with my parents b/c i had to take care of them as they were both not in good health). It was just 2 dates in and i wasn’t ready to talk about something so private and uncomfortable for me. I did clarify my living situation with her after 4-5 dates. She was super sweet and supportive the night I told her. She said it wasn’t a deal breaker for her, thought it was amazing what i did for my parents, and said she felt bad that I felt bad about telling her.We continued dating for another month. One night over dinner with some of her friends, she learned some new things about me relating to my work history. I worked in corporate america after grad school for a while and then started some entrepreneurial ventures. The entrepreneurial ventures were not successful at the end of the day. I put a lot of blood, sweat and tears into it and view them as failures in my life so I don’t get excited to talk about them. I believe she thought I was not open with her about my past because it seemed like she was hearing it for the first time. I believe my not being more open/forthcoming about my work history made her believe I was not an honest person. I can honestly say that I don’t remember if we talked about it in the past and if we did we probably just didn’t go into great detail.I didn’t think anything was wrong that same night because after dinner she invited me to spend the night at her place. I said yes because it was my first sleepover at her place and we hadn’t had sex yet up to this point. We were not intimate that night. She invited me to get naked but I ended up not taking my clothes off since I was trying to be a gentleman. We basically ended up cuddling the entire night and talked. She let me know that I was the only guy she’s had in her bed in over 2 yrs. She asked me if I would ever move back to california to which i replied “only if you’re coming with me”. She also told me in bed that she wanted her own family/kids. I was caressing and stroking her so I wasn’t just lying there. But I wasn’t more assertive because I tried to respect that she wanted to take things slow and that her walls were really high so i didn’t make a move. I left in the morning and gave her a kiss before I left.

A couple days later we saw each other again. We went to get ice cream and went shopping together. We held hands most of the day. During our conversation she said that she wasn’t clear of my work timeline. She asked me how long I’ve been back from California. I told her end of 2005. We then talked about the jobs i had after business school. Then she pressed me on my entrepreneurial ventures but since i don’t like talking about it i started asking her questions to change the topic. She picked up on this but did not say anything that day. 

A few days later she called and said she could not start a relationship based on dishonesty and me not being open about my history whether it’s good or bad. She also said that she knew herself well enough that she would always think that I was not telling her everything. She also said if i want to spend the rest of my life proving to her that i’m trustworthy. She also said that she honestly can’t say what I’ve done for work the last 6 yrs and that when she pressed me about it a couple days ago, it seemed like i was leaving things out and that i turned the questioning to her to change the topic (which i did).

I felt blindsided by the breakup since everything was great up until the end. She showed a lot of interest and said that no one has ever treated her as well as i’ve treated her. She always texted me after our dates and say that she had a great time and can’t wait to see me again. She bought me small thoughtful gifts as I did for her. She wrote me a hand written thank you card for a bday gift i bought her. She also said over brunch a weeks before we broke up that things just seemed to work between us. I’m really confused by the abruptness of the breakup and then her not wanting to meet up in person or chat on the phone to talk about what happened.

I really felt like our relationship progressed to the point where we were ready to have that “talk” about being boyfriend/girlfriend and being exclusive.

Further adding to my confusion is what her last text to me stated. She said that she “really hopes we can stay in contact if and when i’m ready. Who knows… maybe our timing will come back around. You’re a great person. I know i’m going to look back on this and kick myself at some point. I’m really sorry Joe. Thank you for being understanding.” I feel this last message was very unfair to me. I’m really sad how it ended with a confusing text and zero loving communication.I know i’ll never truly know the reason why but I’d love to know whether it was trust issues at play here, fear of intimacy or commitment or that she was in a place where she was ready to settle down and start a family and I was not in that same place yet since I was not independent and was in the process of looking for a job back in corporate america. Or did she run for the hills when she started feeling something for me?


Reeling From a Breakup

Dear Reeling From A Breakup,

There was absolutely nothing you could do to make this relationship work. Unfortunately like many people in the world, you were attempting to progress with someone who just wasn’t ready to let go of the past. She is so damaged to the point that she is unwilling to severe ties with her current relationship with fear-based practices. She has convinced herself that this is the most important relationship of all, as it serves as a means of protection.

I get it. She was hurt, and never ever wants to feel that type of pain and betrayal again. Those who are committed to the relationship with fear-based practices feel that the best way to protect self is to become distrustful, and look for reasons NOT to open up to the love of another. Until she makes peace with her past, and realizes that the actions of her former partner are more than likely a reflection of his deeper issues than a reflection of her flaws, she will continue to sabotage relationships.

As for you Reeling, you must make peace with the decision that you did everything that you could to show her who you are, and pay attention to the red flags. It was only the second date and it sounds like she was drilling you.

I wish you the best.

Submit your inquiries to

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s