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

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.

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.

I (30M) have been in the process of Arranged Marriage, screening prospective matches. Out of all the Women I'd met, there's this one Woman (28F) with whom I'm able to get along quite well. She's quite good in almost all aspects such as Appearance, Personality, Education, Career, Social & Emotional Intelligence etc. and our Interests & aspirations for Future, also align to a great extent. It seems Feasible that we build a Life together. Even she seems to be interested in me. But there's one major problem. She doesn't seem to be Trusting me well enough to open up to me, completely. We've interacting with each other since a Few Months, over Social Media, WhatsApp Messages, Phone Calls & even met each other personally on several Dates & spent good time together, understanding each other. We've discussed almost all the important aspects required for leading a Fruitful Married Life, such as, Finances, Family Affairs, Children, Future Plans in terms of Career & Personal Life, Our Travelling Bucket Lists etc & we seem to be quite compatible on almost all these aspects. But there's one aspect that she's not willing to Share with me openly. That's about her Past Relationship(s) & Sexual History. I had brought up this topic for the first time on a Date, when we'd spent over a Month in Courtship & were meeting each other in person for the 5th time. I started off by telling her that I had not been involved in any Romantic Relationship(s) either Serious or Casual, during my College Years or in my Early to Mid 20's as I had been going through a lot struggles, during that Age and I had started meeting up with Ladies only since the past 2-3 Years, after I was settled well in a stable Career & got Serious about Marriage. And obviously, I am a Virgin. When I asked her to share about her Past, she excused herself & left, abruptly ending our Date. I understood that she might not be feeling comfortable with opening up at this stage. I profusely apologized if I'd crossed my Limits, unknowingly & asked her to meet up for another Date, after a week, wherein I Reassured her that whatever is discussed between the both of us regarding sensitive personal matters, shall only remain between the both of us & need not be shared with anyone else (including Parents). She agreed with me but still didn't open up about her Past. I waited Patiently giving her few more weeks' time to open up as per her Convenience, but she never did. Whenever I brought up this sensitive topic again, she'd either change the Topic or make some Excuse to Leave, ending our interaction abruptly. I still maintained Patience & kept Reassuring her gently, that I want to know about her Past, not to Judge her, but only to understand her better. Still she seemed reluctant to open up about her Past, but is actively conversing on any other Topic. The last time we'd met personally was on a Dinner Date, a week ago. When I gently raised the Topic again, she seemed to get somewhat irritated & asked me "How does my Past, really matter to you?" I Replied that it is very much important for me to know everything about her Past, to be able to Trust her completely & take the Relationship ahead and once again I reminded her of both my Promises that I would listen to her with empathy & understanding without Judgement and that I would maintain utmost Secrecy with Respect to her Sensitive Personal Matters. Still she seemed avoidant about the Uncomfortable Conversation & tried to Gaslight me as if I'm Disrespecting her Personal Boundaries. Our Date ended on an unpleasant note & since then our Interaction over WhatsApp has been just minimal. I don't understand what's the matter with her, she never Shied away from discussing any other Important topic & communicated her views, quite effectively, giving me the Impression that she's a Matured Person, but I don't understand why she's so reluctant to open up on this Important topic, in spite of repeated Reassurances from my side. Please advise me, how do I proceed with this Sensitive issue? I am very much into her & wouldn't want to throw away such a Wonderful prospect as we seem to be getting along, quite well, with each other. At the same time, I feel the need to know everything about her Past Relationship(s) including her Sexual History, so that I can be sure about certain things, which greatly matter to me. My Gut Instinct refuses to Trust & Accept her completely, without this missing piece of Jigsaw Puzzle. I'm in great Dilemma now, any Qualitative Advice from Experienced People would be greatly appreciated.