LittleWay84, I’ve read all your posts in this thread and the posts to you. I’m with the many here who think you are doing just fine listening to your instincts on this. The fact is we are saturated in a secular mindset about dating in the world today and for it to have affected the attitude of some men who see you in the parish is no surprise. The 40ish guy’s friend is particularly creepy and it might do you well to say to the unwelcome matchmaker directly: “Please stop. I don’t like that at all.” If he makes such comments in front of others you can correct him in front them, be it your mother, the priest, or anyone else, “I find that kind of attention unwelcome. Please don’t do that any more.”
I had a bad experience with a first marriage, and after that fell apart, I was a young Mom and did not want to date especially since the ex was living with his paramour, and I wanted our child to have one parent that was all-in. That was a priority, and also I realized that I sure made a mistake picking that husband, and I did *not *trust myself to *ever *pick one again. Perhaps God wanted me to stay single all of my life? I made up my mind to NOT DATE, maybe forever, until I was sure what God wanted for me. I thought perhaps He might want me to be a nun someday, so, I better learn to be happy alone in case He wanted to call me that way some day.
And being an alone single parent was oftentimes lonely, as I am sure sometimes in different ways your life is lonely at times, too. However, God sustained me, as I know He is sustaining you, and will continue to.
At the end of my child’s high school, shortly after a dramatically major emotional/spiritual healing, that I had felt God call me to seek, that took place over the course of a weekend, I met and fell in love really hard and really fast with my now-husband. I was not looking to date, in no way, and he did not seem like someone I would have picked to date if I were picking! But it was out of my hands, truly God did this thing that I did not pick… We had many obstacles, which began to fall as it was clear this was God’s will. We were married in the Church less than two years ago and not one day has there been a doubt that God wants us together. We are so happy. Although I had seen long-happily married couples, I just never imagined I could be one. Never pictured it. But its us, and its pretty amazing.
God really is the best matchmaker, and so I suggest you go with him.

It really worked for me! No dating at all. This is not for everyone, but I knew it was for me (I dated plenty in college. I really had a pick who to marry. And I picked wrong. This time I wanted to be QUITE sure
God picked). You have to decide what is right for you - not-dating was my choice, and what is your boundary is your choice. Going with
not dating anyone unless you really feel right seems like a good suggestion under your circumstances. You can always just be quick to say “No, thank you” if something doesn’t feel right, since you can usually go back and change your mind anyway. Yes, take a “just say no” attitude if that’s what your instincts are telling you, and you don’t owe anyone an explanation for why you are disinterested. You can always say a prayer after, “God, if that was not what you wanted, please make it clear.” If you are trusting Him with your dating life, and
you want Him to be clear, He will be unquestionably clear!
God was clear with me. His timing was different from mine. I figured dating for me, if God did not want me for another vocation, would be not till my child was done with college and married! Also, I thought God would be more methodical about showing me my husband. I expected, far in the future, it would be like a nice Catholic man showing up at my door one day saying, “God wants us to marry” and I would say, “I don’t think so” and he would go about proving God said it, somehow. I completely did not expect that it would be me falling completely hopelessly in love. I truly was not wanting it at the time, and tried to *will *it to go away, but I could *not *make it go away. I was confused at first, but God had ways of assuring me that this was all-okay by Him.
Also my husband wasn’t looking for anyone, either, I should say. He just accepted his lot in life, which didn’t look so very great at the time I met him. But he had prayed the shorter Divine Office (not so short!) every single day and The Angelus 3x a day for nearly 30 years, and I think you j
ust can’t out-give God in generosity.
Also I want to say that God’s clock is even better-timed than your biological one, too, so I suggest you give Him your clock, too. That’s a
lot to trust Him with, I know, but I am confident He won’t let you down with anything you entrust Him with.
Behold,
I send you forth as sheep in the
midst of
wolves: be ye therefore
wise as
serpents, and
harmless as
doves. - Matthew 10:16
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