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Should I be worried about her past? Connecting with a woman despite my insecurities - Advice Needed

Kanchan Rai |512 Answers |Ask -Follow

Relationships Expert, Mind Coach - Answered on Jan 29, 2025

Kanchan Rai has 10 years of experience in therapy, nurturing soft skills and leadership coaching. She is the founder of the Let Us Talk Foundation, which offers mindfulness workshops to help people stay emotionally and mentally healthy.
Rai has a degree in leadership development and customer centricity from Harvard Business School, Boston. She is an internationally certified coach from the International Coaching Federation, a global organisation in professional coaching.... more

Asked by Anonymous - Jan 16, 2025Hindi

How do I 32M get over my insecurity with 30F? (Seeking Advice) Met this girl via matrimony exactly 2 months back. We connect well. Our families have met recently and it went well. Somehow we found a lot of connections between our families. That's just a bonus. Her family likes me a lot and they wanted to do Roka when they met us last week. I had told her, that no matter our bond, we should talk a lot and give it 3 months before going for roka. We live in different metro cities and have met twice now. About her: She is 30, well behaved & spoken(most important thing for me), smart, good looking, and is extremely polite. She is an army brat, has had a lot of freedom from family. Due to her father's job, they kept getting posted to different cities so she doesn't really understand family part of things. She's in a IT job. About me: I'm 32, okayish guy, in IT. To take things ahead I need to know my partner's past. I have no judgements at all but need to know stuff. Getting to know things over time bothers me a lot. I've tried to work on it, and have always made sure I don't bother the other person too much. After a month of talking, she told me that she had a casual boyfriend for an year. All her friends were dating in Bangalore and she decided to try it out. Found a guy through bumble and started dating him. So, according to her there were no feelings, just a person for her to go to places with, have drinks, and party. She likes drinking a lot and I have never taken a sip. She said that it was just a phase and she was immature. This happened between 2018(Nov) to 2020(march). So, it's been like 5 years. Never dated anyone after that. Since covid(2020) she's been living with her parents due to wfh. I have been completely ok with that but new things surfaced and they are messing with my head. While snooping around her facebook I figured out who that person was and this guy is super close to a person in my distant family. In fact they both were flatmates until their respective marriages. This distant cousin of mine knows me and knows her really well. These 3 used to hangout a lot and he has seen her come to their flat regularly. Infact, she had a good bond with my cousin as well. There are things that bother me and I really can't shake things and feel super awful in my gut. She mentioned that she and her ex had a common love for drinking and regularly visited pubs, got drunk, and partied. This means that they would be staying at each other's place as well. This is something super old but bothers me a lot. Specifically the fact that she would be drunk partying with someone for an year and sleeping with him, with no feelings. Secondly, I found some posts where she has liked a post about this guy on fb/insta from mid-2021. I have already confronted her twice to share everything and we shall never discuss this again but this bothers me a lot. Secondly, now that I know the timelines I can figure out what photos have been taken by her ex. There's even a photo of her sitting on a messy bed, where she's cutting her bday cake. They celebrated it together. I found my cousins page and some other pages from which I knew it's the guy's room/flat. I know everyone has a past. She has come clean to me but somehow my brain is so split. Sometimes her nature and behaviour with me make me not care about anything. And then I know the bed, flat, and her actions with some guy. Then there is this angle where the ex's flatmate is my distant cousin and knows about her well.

Ans: What you’re experiencing is completely valid. It’s not just about the fact that she had a past relationship, but also about the details—knowing her ex was deeply connected to your distant cousin, imagining their time together, and realizing that those experiences once meant something in her life. It makes it feel uncomfortably close to home, which is why it’s so hard to shake off. It’s not about judgment, but about the emotions that these thoughts stir up within you.

The truth is, the past cannot be changed. She has been honest with you, shared what happened, and reassured you that it was a phase in her life that she has moved on from. The fact that she hasn’t dated anyone in five years and has been living with her parents shows that she is in a very different place now. But your mind keeps looping back to what once was, and it’s preventing you from fully embracing what is.

Right now, the biggest challenge is not her past, but your ability to be at peace with it. You have to ask yourself—are you willing to let this define your future with her? Because if you can’t fully accept it, these thoughts will continue to surface and create distance between you. A part of you clearly wants to be with her, but another part is struggling to detach from these mental images of her past.

Instead of confronting her again, take some time to reflect on what truly matters to you in a partner. She has shown you who she is today—polite, well-behaved, mature, and emotionally present in your relationship. She has not hidden anything from you, and she has moved forward from that phase of her life. The real question is whether you can do the same.

If you feel this is something you cannot get over, it is better to step away now rather than carry these unresolved emotions into a lifelong commitment. But if you genuinely see a future with her and believe in her as a person, then it’s time to start training your mind to focus on the present and the relationship you are building, rather than a past that no longer exists.

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Anu Krishna |1465 Answers |Ask -Follow

Relationships Expert, Mind Coach - Answered on Nov 23, 2022

Question by PB - Nov 23, 2022Hindi

Hi Anu,Myself Praveen. I appreciate your writings on Rediff. First of all thanks for that.I would like to ask guidance or your thoughts on establishing a relationship with my lady friend. I met her 4 years back in my old office and we got in company soon and started talking and somewhat share most of the personal s***s too. I started having feelings for her. I mean I wish to have a marital relationship with her because I am very comfortable with her. But I was unable to make any move or feared of losing her company if I tell her my love.That time I never knew her age. Later I moved from that job to pursue some personal goals so I moved to some other place without the knowledge of my own family. The only person who knew about it was her. She stood with me and emotionally supported me and was knowing that it was my strong wish of having that dream/goal. We were in touch as nice friends. Her phone calls were happy moments for me because I was alone at my new place where I'd gone to pursue my dream. Someday she called me and during call she was upset. That day she shared some of her personal things and during the conversation I realised that she is 8 years older than me and she is at her mid 30s. Firstly, it was like a shock for me. I wondered why a beautiful girl like she not got into a marriage or any other serious relationship still that age. Okay, that doesn't matter me. However, knowing about most of the complexity in this partnership including support from both family or cliche society thoughts; I decided to have her as my life partner. But still I am not able to make a move like that. Somehow, I had to come back to my homeplace and sorry to say that I failed to pursue my goal which was bit depressing. Still I couldn't make a move to talk her about this. I am getting an odd feeling that she treats me as a brother or a nice friend only. I am confused when she calls me bro. Some days ago she told me that I am her good brother. Frankly I don't like her calling me bro. I still love her and I always see her as my life partner.The thing is I fear that I may lose her company if I express my love for her. Also I fear that she may emotionally get low if she really considering me as her brother. I don't want to give her any pain, but meanwhile I couldn't miss her in my life. Nowadays, we rarely talk on phone or meet because some of her professional engagements. That is not a problem for me. I respect her as well as her personal space. Only thing I want is to communicate her about my mind and having a relationship with her. I know she might also be concerned about our age gap as well as what society may say, but I don't care such rubbish. I strongly believe that I can be a great partner. Share your thoughts on making an approach without giving her any emotional pain or trauma.

Ans:

Dear PB,

Thank you for your kind words on my writings and columns. Highly appreciate it.

I cannot assure you of the fact of her not having any emotional reactions. Her reactions are not something that you can control.

The easiest way to resolve this confusion that you are going through is to simply express it. It’s similar to how children are.

Have you seen them say things without a filter and unfazed by how the other person will react?

Then along came the adults and asked them to keep quiet and then the child in us grew up to become a recluse and ignore our own feelings.

I agree there is an etiquette and social norms to be followed as adults but to not be able to express our feelings is nothing but conditioning from our childhood.

And what did it teach us? It taught us to avoid the rejection and ensuing disappointment.

That’s exactly what you are running away from; all the rejection that may happen and the disappointment from that.

But what use is that love if you can’t express it for fear of rejection. If you feel so strongly about it, approach it boldly and very gently.

Yes, it may shock her and it’s possible she has no feelings or sees you as a brother, but at least you know where the connection stands.

Now whether she is going to be hurt or not is a question of how emotionally mature she is.

So, before you start the conversation, do request her to hear you fully and not judge you for your honesty. This may ease her shock and help her respond rather than react to you.

On your part, keep your expectations to a low and smile through the situation. It helps lighten the load that you might be carrying.

All the best!

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