u/ThePatio

41m, I have 5 kids, one grown and 4 ages 16–12 that are supposed to be 50/50 custody. I know this limits my dating pool, and my last relationship ended I believe in part because she “didn’t want to be a step mom” and was looking forward to empty nesting herself. Recently my ex wife has made some bad decisions and can’t find housing. She’s talking about giving me full custody. How bad are my dating chances going to be out there?

Met my ex after a month of no contact, aside from crossing paths once. She was the dumper. Texted her, asked her to lunch to catch up. She agreed to have lunch as friends. I went in with the intent to just catch up and try to lightly test the waters. She dropped the heavy stuff into the conversation, asked if I’m dating, (I tried but realized I wasn’t ready, and she said she’s not at all either), asked about what’s going on between me and my ex wife who has been around a lot for various reasons (there’s nothing). She also asked if I was doing better, the last we spoke for real I was pretty devastated, and I kind of pivoted away to talk about the other shit going on in my life (like with the ex wife and her nonsense). Other than that it was pretty normal conversation, actually catching up. Some accidental physical contact that wasn’t too awkward, and not immediately rebuffed. She told me to let her know if I want to hang out in the future. I told her the same thing. Question is, where do I go from here? How long do I wait to contact again? If she’s asking those relationship questions, is she holding the door open a little?

For background, we dated three intense months before she broke up with me at the end of April, saying she didn’t see a romantic future with me. I was devastated. I thought she was the one. (It’s also my first relationship after ending a 16 year long marriage so take that as you will but she is definitely an amazing woman) We met a week after that (and once in between to exchange our stuff). When we met, we talked for probably an hour. I don’t remember getting more than a vague “I don’t feel the connection as strongly as you” or there’s “not a spark” as reasoning. I pushed back and said her behavior when we were together didn’t match what she was saying, but I asked her about three options. One which I knew was probably going to get discounted right away, was we get back together and figure it out. Second was maybe sometime in the future. Third was if she felt nothing more at all, in which case I would drop it forever and not ever bring up getting back together again. She opted for number 2, stating that she couldn’t predict the future. We parted amicably, but from that day I went no contact, barring one time we crossed paths a couple weeks ago. Today I broke no contact. Sent a meme I thought she’d like, asked how she was doing. Her response was brief, didn’t mention the meme and asked how I was doing. I told her I was doing good, and asked her to lunch this weekend, specifically to catch up, with no expectations or pressure. She replied “only as friends”. I said of course, and we hammered out the rest of the plans to meet. I’m perfectly ready to be at peace with however this turns out. I plan on keeping it light and not talking about the relationship or why it went wrong. But I can’t help but wonder if this was the right thing to do, or if I made a mistake. Thoughts?

Been no contact for two weeks now, broken up with for 3. We were only together for 3 months but for some reason I completely fell for her, and her sudden, “I don’t see a romantic future” right after a romantic vacation and 3 intense months completely broke me. I was doing ok the last couple days, until today, and had to deal with some other personal unrelated issues. Now I just want to hear her voice. I told myself I’d wait a month. My mind is cascading with both her and this other shit I’m dealing with.

We only dated for three months too, which makes me feel stupid and crazy for feeling this way. She ended it the day after we got back from an idyllic vacation. In the week that followed I felt like my life collapsed, I lost over 5 pounds, couldn’t sleep, can’t think of her without immense sadness. I asked to speak with her, for closure mostly, and the forlorn hope that something might be salvaged. We spoke, we laughed a little, I cried more than a few times. We were very compatible, talked for hours, never argued in our relationship, but for all the good times we had, she never felt enough of a spark. We parted on good terms. She left open the possibility of something in the future, and while she’s a good, honest woman, I can’t help but feel she’s letting me down gently. But I did tell her, if there’s no chance, just be honest, I’ll drop it forever. So idk. I’ve felt with heart break before, both with women who didn’t deserve my love and women who I didn’t deserve. But in my 40s after 3 months? What is wrong with me?

Yesterday I was broken up with a woman I’ve been seeing the last three months. She had met my kids, and I hers, she also met my parents, friends, and just this past weekend we went on vacation together and had a wonderful time. We never fought or argued once. We had similar values and interests. But after all that she sent her “dear John” letter via text, basically stating she didn’t feel a real connection with me. The day after we got back from that great vacation. She told me I did nothing wrong and I was a great guy.
In retrospect it didn’t come entirely out of nowhere. Early on she mentioned I might be more into her than before than vice versa, but she was always more than happy to spend time with me, have emotional and physical intimacy, and do real couple stuff together. We had both gotten out of long term relationships last year. I figured she just wanted to take it slow, and since she had so recently been hurt she was looking to avoid being hurt again. So I tried my best to show her I wouldn’t hurt her, was always open and honest. Respected her boundaries, set some of my own. She did say early on she wanted to keep it casual, and limit our time together, and we were both in agreement. I had to focus on other things like my kids and not spend all my time on a new relationship as well, but we usually spent 2 to 3 days a week together, even if it was something short like a lunch and a walk.
I guess I want to know, how after all that, how someone does not have a “real connection” with someone else. I get being afraid of commitment, I’ve been there, and I don’t feel like I was pushing it, I always said let’s just play it by ear. I wasn’t rushing things, at least in my mind. The main issues she had (which she did not mention in her text, but in early conversations, was the number of kids I have and that she didn’t want to be a step mom (which I told her I’m not looking for a step mom for my kids) and and the income disparity (she makes almost double what I make but we always took turns paying for meals and outings).
I don’t understand how a couple that never fights, can always talk and never has a dull conversation or a problem talking, does all these things together, and has good physical chemistry, and one person still doesn’t feel a connection.