These Last Two Hurt - Where to Go From Here?

I'm 34/M and have been on OLD for 10 years (been on everything short of Tinder, including Catholic focused dating sites). Most relationships (as others have experienced) have been short, save for four where the other person was emotionally unstable, wanted a "trophy", or needed "saving" (I ended one such relationship a year ago). I've been ghosted, stood up, and told many times that the woman didn't see me as anything more than a friend (or even given some weird excuses). Granted, I'm not the most socially confident person sometimes.

The last two dating partners have definitely brought out some frustration.

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- The first (slightly older, Catholic like me, and divorced) met with me for four hours after going to church together, and we had great conversation. However, she seemed to be always busy when I tried to schedule Date #2, and I had a few business trips as well. She said not to worry and that we weren't in a rush, but she later texted me saying she saw us more as friends and was in more of a hurry for sex & children than I was (we discussed this - I was waiting for the right person and she had been divorced). When I expressed confusion given her earlier comment, she curtly replied and said "to each his own".

- The second wasn't Catholic but she was Christian (important to her) and she seemed to have her head on straight. We went on several dates and she seemed to enjoy me, as she was eager to meet up again. She was quite sarcastic but seemed to take my slightly more dry banter. I saw her before a trip to London for work, and she and I were texting through that. However, the last few days, she has been significantly slower to respond and her texts have been much shorter (with no detail or sarcasm). I asked if everything was OK last night and have not heard back since. I am beginning to think she, too, is ghosting me. I had even bought her a little token from my London trip that now will probably go to waste (because I can't just say I was saving a Paddington bear for years in hopes to give it to someone).

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Whenever I face rejection like this, I begin to wonder what I am doing wrong (if anything). I'm rather mature for my age and my parents seem to think this is generational and a side effect of online dating, but I am not as quick to blame the other side completely. Of course, no date will ever give you feedback to improve yourself, and I have few close friends who know me well enough to be honest. I've started doing Meetups (though haven't found many women who are single or my age/type yet) and am active on three apps (CMB, Bumble, The League) plus I pay for Match & CatholicMatch, which all have low hit rates. I'm always nervous approaching a woman cold IRL because I assume they are already taken or aren't my type. I'd love coaching or matchmaking to at least confirm if I'm doing everything right, but paying thousands for no guarantee of success seems crazy. Expanding my net beyond my major metro area is an option, but then you are getting into areas (NYC) where the pool is so big, a long distance relationship might not be attractive (plus I fear the travel would wear on both of us).

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Anyone have any suggestions on what else I could be doing?

Submitted May 07, 2019 at 08:02PM

I'm 34/M and have been on OLD for 10 years (been on everything short of Tinder, including Catholic focused dating sites). Most relationships (as others have experienced) have been short, save for four where the other person was emotionally unstable, wanted a "trophy", or needed "saving" (I ended one such relationship a year ago). I've been ghosted, stood up, and told many times that the woman didn't see me as anything more than a friend (or even given some weird excuses). Granted, I'm not the most socially confident person sometimes.The last two dating partners have definitely brought out some frustration.​- The first (slightly older, Catholic like me, and divorced) met with me for four hours after going to church together, and we had great conversation. However, she seemed to be always busy when I tried to schedule Date #2, and I had a few business trips as well. She said not to worry and that we weren't in a rush, but she later texted me saying she saw us more as friends and was in more of a hurry for sex & children than I was (we discussed this - I was waiting for the right person and she had been divorced). When I expressed confusion given her earlier comment, she curtly replied and said "to each his own".- The second wasn't Catholic but she was Christian (important to her) and she seemed to have her head on straight. We went on several dates and she seemed to enjoy me, as she was eager to meet up again. She was quite sarcastic but seemed to take my slightly more dry banter. I saw her before a trip to London for work, and she and I were texting through that. However, the last few days, she has been significantly slower to respond and her texts have been much shorter (with no detail or sarcasm). I asked if everything was OK last night and have not heard back since. I am beginning to think she, too, is ghosting me. I had even bought her a little token from my London trip that now will probably go to waste (because I can't just say I was saving a Paddington bear for years in hopes to give it to someone).​Whenever I face rejection like this, I begin to wonder what I am doing wrong (if anything). I'm rather mature for my age and my parents seem to think this is generational and a side effect of online dating, but I am not as quick to blame the other side completely. Of course, no date will ever give you feedback to improve yourself, and I have few close friends who know me well enough to be honest. I've started doing Meetups (though haven't found many women who are single or my age/type yet) and am active on three apps (CMB, Bumble, The League) plus I pay for Match & CatholicMatch, which all have low hit rates. I'm always nervous approaching a woman cold IRL because I assume they are already taken or aren't my type. I'd love coaching or matchmaking to at least confirm if I'm doing everything right, but paying thousands for no guarantee of success seems crazy. Expanding my net beyond my major metro area is an option, but then you are getting into areas (NYC) where the pool is so big, a long distance relationship might not be attractive (plus I fear the travel would wear on both of us).​Anyone have any suggestions on what else I could be doing?