2 mo

A surprising chapter of OlderAndWiser's dating history!

OlderAndWiser u

In March, 2015, after a three month separation, my divorce became final.

"Okay, youre free to go find your next victim."
"Okay, you're free to go find your next victim."

It was a relatively short-term marriage with no children and we agreed on all of the terms of a divorce. So it was over quickly and I was single once again.

A few months later, I subscribed to a few online dating sites and started perusing the available women.

"Hello, I love you, wont you tell me your name?"
"Hello, I love you, won't you tell me your name?"

I contacted a woman - Millie - who was reasonably cute and who had some interests in common with me, so we talked on the phone once or twice, then arranged to meet for dinner. At dinner, I was rather smitten.

"There must be SOMETHING wrong with her!  Am I dreaming?"
"There must be SOMETHING wrong with her! Am I dreaming?"

Maybe that happened because she was the first date I had in the past 7 years. In any event, I thought she was attractive and she had an effervescent personality, but during dinner, she made a comment that caught my attention: "you might not like me any more when you get to know me better." I wasn't sure what she meant but it could possibly mean that she was married to someone else or still in the process of a divorce. I DO NOT date married women!

So I went home and I started looking for information about her. Since I am an attorney, I have access to court records and that is the first place I start when I want to know more about someone. Wihin minutes, I learned that, before 2005, she had an extensive record of charges for drug possession, DUI, and prostitution . . . but she was single. She had been married but her husband had died around 2010.

A surprising chapter of OlderAndWisers dating history!

I have never dated a prostitute, never visited a prostitute for "business" purposes, and would never go looking for a prostitute to date, but I had already met Millie. And her criminal record had abruptly stopped around 2005.

I talked to my best friend, a man who has known me for 50 years, and asked for his advice. He was concerned, of course, but not judgmental and suggested that I determine for myself if she had truly rehabilitated herself. I agreed with taking that approach.

A surprising chapter of OlderAndWisers dating history!

The next time that I saw her, I didn't mention the information I had discovered. I decided to wait and see if she would reveal that without me mentioning the topic. Around our third date, she started with "There's something I need to tell you . . ." and I knew what was coming. After she revealed the story of her past, with many more details than I already knew, I advised her that I was already aware of her past but had not disclosed it in hopes that she would volunteer the information. I was relieved, and I told her I wanted to continue dating her. She then told me that, despite her past, she was not quick to jump into a sexual relationship and I told her that I was attracted to her but respected her decision.

Those orange cushions are ugly!
Those orange cushions are ugly!

We continued to date for a few months, and on one occasion, she even spent the night with me, though she advised me in advance that she was still not ready for a sexual relationship. We spent that night in the same bed, and went to sleep snuggled together, but there was nether hanky nor panky between the sheets.

I snore loudly but she was deaf in her right ear.  A match made in Heaven!
I snore loudly but she was deaf in her right ear. A match made in Heaven!

We continued to date for a few months and ultimately broke up because she kept making excuses to not spend time with me. She claimed that she was too busy but she was really no busier than I was at that time. Whatever the truth may have been, it was obvious that she was not committed to the idea of being in a committed relationship with me . . . and since I was recently divorced, I had no problem with telling her that we could go our separate directions.

It wasnt this dramatic;  we had only been dating about two months.
It wasn't this dramatic; we had only been dating about two months.

If I had done my research and confronted her with it on the second date, how would things have progressed? She probably would have felt embarrassed, gotten defensive, and that would have been the end of things.

I still think about her on occasion and I have even seen her once at the place where she was working (BBB.) I never contemplated trying to rekindle anything with her but I remember her wih warm regards.

A surprising chapter of OlderAndWiser's dating history!
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Most Helpful Girls

  • Daniela1982
    This may just my opinion, but I think she thought you were above and more classy than her and that she didn't deserve such a great guy. When you have a checkered past you often think that you are not good enough for anyone except the same losers club that you perceive yourself to be a member of. Plus you don't really know what her journey was about or what it was still bringing to her, or how it was holding her back. Nor will you probably ever know. But from what I have read at least you weren't judging her and you were accepting of her baggage. Unfortunately, you can't help those that think they are beyond help, or to cure their self hateA surprising chapter of OlderAndWiser's dating history!.
    LikeHelpful 6 People
    Is this still revelant?
  • SaoirseS
    @OlderAndWiser. Thanks for sharing! I'm always glad to see that even when things don't work out, people can remain amicable.

    I've thought of sharing some of my dating experiences here, something along the lines of "dating: when you're not Asian enough" because that's how some of my dating experiences have gone lol. Maybe one day I will, but a lot of people seem overly touchy about race/ethnic background right now.
    Like 2 People
    Is this still revelant?
    • Not me, as my girlfriend is a 58 year old Chinese woman who came to the US 30 years ago. I don't care about the racial issue, as long as we are mutually attracted and compatible, but I have a step-father who is an idiot of the highest order so I understand what you are addressing.

      His grandson married a girl from the Phillipines and, at the wedding reception, he asked his grandson, "What's wrong? Couldn't get an American girl to marry you?" When I showed him a picture of my current girlfriend, the instantly said, "She's not very pretty, is she?" When my mother chastised him for the remark, his defense was "It's what I thought, so I had to say it." The idea of keeping his mouth shut and not hurting the feelings of others is "foreign" to him. I have only taken Miss Helen around him twice and I was constantly on guard both times.

    • SaoirseS

      With me, it's a matter of being a clone of my Japanese mother, but looks is where it stops. I was born and raised in the Midwest US, and my mother was well Americanized by the time I was born (she was 41 when I was born, and my brothers are much older). Truth told, I get very few comments about being distinctively Asian in appearance; I actually get more ribbing for being short and petite. Having said that, I seem to attract a lot of guys who are fascinated with Asians and all things Asian and they seem disappointed because I don't act Asian enough. I'm the opposite of shy and submissive and other stereotypes about Asian women. A few months ago I started dating a guy who took me to a Beni Hana on a first date and was surprised that I chose to eat with utensils rather than chopsticks. He spent a lot of time telling me about his travels in Asia, and it was pretty clear to me he knew more about it than I did. With me the looks don't match what people expect, but sometimes I have a little fun with it with those who can take a harmless joke. Your girlfriend sounds lovely. I can tell from your previous posts that you're a good match. Hope things continue to go well for you! :-)

    • Thank you for your comments. Yes, she has become somewhat Westernized but she is still distinctively Chinese. I have dated women on many different nationalities over my lifetime (Ukraine, Poland, Germany, Ireland, Brazil, Colombia, Phillipines, China, India) but I have never sought women just because they look different or I'm fascinated with their culture. In fact, I think the cultural differences make relationships more difficult, so a lady being from another country is not an added bonus but more of an obstacle.

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What Girls & Guys Said

216
  • AimeeKyle
    Great story. Thanks for sharing.
    Like you, I would have waited for her to share her past.
    Unfortunately sometimes things don’t work out and we have no idea why. You were in a good place to accept the outcome without an explanation/closure. For me that has come with age. Closure is still a nice to have not but not necessarily a must have.
    Like 1 Person
  • worldscolide
    Interesting story. I get why you left though. Most women who work as sex workers, Be it prostitution or really anything else aren't capible of being in committed relationships. Personal experience with it, through my mother and a few strippers i was friends with taught me that. There is nothing wrong with it though. If you're the kind of guy that wants a committed monogamous relationship though sex workers are definitely not the way to go. I am however glad you remember her warmly.
    Like 1 Person
  • Shawn411
    Interesting weather you two are made for each other is not the main question it is men do not like to be strung along about having sex and you are always wondering how come you don't have a man?
    Like 1 Person
    • As long as a woman is straightforward with me about sex, I can be patient. . . as long as what she is telling me does not sound like an excuse. I have waited as much as three or four months before having sex, but I have also had relationships that became sexual after the third date.

    • Shawn411

      Great we are only human remember that song?

    • Hell yeah, remember that song.

  • bamesjond0069
    You made a mistake accepting her excuse for not having sex. That makes sense if she's a virgin or only been with her ex-husband who she's now divorced from, it makes zero sense for an ex prostitute. She was showing you her mental illness right there. Its a form of magical thinking. You could have forced the issue and broke her messed up thought process or if it didn't work ended the relationship right there.
    Like 1 Person
  • msc545
    If you could do it all over again, what would you change? Sounds like perhaps you put some time into this.
    Like 1 Person
    • I would try to hold back on liking her so quickly. Although I initiated the breakup, I was really saddened to do that as I really liked her. . . when she had time for me.

    • msc545

      Why do you think the two of you broke up if you know? It was not clear to me from what you wrote.

    • I'm not sure that I know the real reason. What she told me was that reasons why she could not see me when we had previously made plans. "I was so tired after work that I just went home and went to bed." At that time, she was 54 years old and working a retail job. I was 60 years old, practicing law, and she couldn't keep up with me. It felt like excuses, but she was upset when I broke up with her.

      I have had a few relationships with women who occupied a much lower "station in life" and sometimes the discrepancy in education and income makes them feel inadequate and they assume that they are just a temporary diversion for me. That may be closer to the real reason, but I'll never know.

    • Show All
  • Likes2drive
    You always have interesting relationship stories, my divorced was finalized in August 2016, we agreed on everything too but we had kids so it made it a lot more complicated and high child support. But that’s done with now, It’s still a challenging thing dating, so far it only got as far as being friends or some scammers online. Still trying to be positive though and talking to another potential but then it’s getting close to Christmas and wonder how that will work if we get that far. I think I remember you having a question like that way back.
    Like 1 Person
    • Excellent recall. I met my current girlfriend for our first date on December 15 last year. She was living in Gainesville and I live in Jacksonville, about 80 miles apart. Our second date was a week later, also in Gainesville, and then she came to my home for dinner and fireworks on New Year's Eve. We did not exchange Christmas gifts last year. Now she's living with me.

      She is not big on gift but I have a special gift planned. We both cook, so I ordered an apron for me that will be embroidered with my name and "The Boss" embroidered below my name. I have a matching apron for her which will be embroidered "Helen. . . The REAL Boss!"

    • Shawn411

      Ok thanks for reading my opinions 🙂 as im older now it's like a gift that im willing to understand holla baby 👶 😘

    • Oh ok, I was wondering how that worked out, yeah I guess I will see how it goes first. Actually it doesn’t surprise me with her since she is Chinese, my brother has been married for 6 years now to a Chinese woman right from China and their customs are different in ways we are not used to, like they never say I love you to each other, took my brother awhile to get used to that because women here always want to hear it

    • Show All
  • BillyBalls
    First. If she broke things off let it be.


    As to her background, female drug addicts often turn to prostitution to support their addiction. So it wasn't a career choice made with a clear head.

    However, many men can't get pass that type of behaviour.

    Hopefully she didn't go back to what she was doing.

    I knew two female addicts. When I first met them I looked down upon them given their past.

    But over time we became good friends.

    Unfortunately both relapsed and died within 6 months of each other.

    When the second one died it hit me like a ton of bricks. I actually came to care a lot about both girls.

    Hopefully the woman you know does well!!!
    Like 1 Person
    • I don't think she has relapsed based on me seeing her at the same job a few years ago, but I haven't heard from her since then

  • spartan55
    "there was neither hanky, nor panky between the sheets" 😂 😂 Love it.
    Like 2 People
  • Jamie05rhs
    "She claimed that she was too busy but she was really no busier than I was at that time.".
    I think this is a common thing that women do. If you don't tell them everything that you are involved in, they tend to assume that you aren't involved in anything. Maybe it's more of a problem with guys who are more discreet and humble; I don't know. Also, if it's something stressful or difficult going on, we tend not to talk about it; because we as men have been raised to be tough and stoic and not complain about things. So that's why she may think that her life is more difficult than ours and she may get the impression that she's "busier" than we are. While all the time we're bending over backwards to be available for her, simply because that's the courteous and gentlemanly thing to do.
    Like 1 Person
  • WhiteBoyChill
    I don’t think I could date a woman with such a troubled past. I find the details of what she did so disturbing I almost can’t see past it.
    Like 1 Person
  • Hotboy_booblover
    Nothing u did changed the outcome.. sometimes things don't happen for no reason.. thats my opinion.. I m sure older and wiser knows better
    Like 1 Person
  • loves2learn
    Really interesting story. Thanks for sharing!
    Like 1 Person
  • Browneye57
    Such a nice story for such a bimbo. Oh well.
    Like 2 People
  • exitseven
    pretty amazing story,
    Like 1 Person
  • Massageman
    Thanks for sharing your personal insights!
    Like 1 Person
  • DaveToo
    Thank you for sharing!
    Like 1 Person
  • Sam2021
    Interesting, thank you for sharing.
    Like 1 Person
  • Anonymous
    You were too nice for her. Despite all the talk about changing and putting her past behind her, wanting to find a nice guy, girls like her are still only attracted to degenerate fuckboys. You never stood a chance and really should never have considered it in the first place.
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