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Dating : Dating Consistently for Three Years, and I’m Losing Hope

Dating : Dating Consistently for Three Years, and I’m Losing Hope


I’m a 27(F), and I’ve been heartbroken by online dating too many times to count. If I’m giving an honest assessment of myself, I’m kind of a catch. I’m pretty cute, active, doing great financially and with my career, fun, great cook, kind, bright, with lots of interests. I’m really who I want to be – I mean, I’ve got things I’m working on, but I feel really happy with where my life is right now. I find it easy to make friends, and my life is full of people I love who love me. Except romantically. I’ve been single for over three years now, and it’s been the same story again and again. I’ll go on a few dates with someone I think is really a great match. Conversation is easy, physical attraction is great, we share the same values and relationship goals.

Then, it’ll happen – sometime in between the “getting to know you” stage and the “we’re a thing” stage, I’ll get the text. He needs time to work on himself. He’s just not feeling the click. He’s realized he’s not quite over the ex.

I am crushed, because I’ve just started feeling like we could be something together. After this happening repeatedly, constantly, over the last three years, I’m starting to lose hope. I can’t seem to bounce back. Every time I let myself like someone, it’s haunted by this feeling that I shouldn’t, because I’ll just get hurt. Every time I see a text from a date, a little voice in my head has started saying, “this is it, it’s the one, he’s ending it.”

I hate that I’m approaching dating with this anxious little voice in my head. It’s even worse because the anxious little voice has been right so often that it’s no longer so little. I used to be a really securely attached person who had a lot of fun with dating- who could say, “well, that’s unfortunate, but must not have been meant to be” when it didn’t work out. Now, it’s turned to, “of course it didn’t work out – you knew it wouldn’t work out, because it never works out.”

Does anyone have any advice to help me get some peace with the process? Words of encouragement?

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What do you think?

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  1. It’s easier said then done.

    Not everyone you date will end up in a relationship with you. Don’t be too hard on yourself, a lot of the reasons why they might break it off likely have nothing to do with you as much as it has to do with them.

    Dating is hard. Period. It’s hard enough to find someone you click with but it’s even harder to push it to the next stage.

    You will eventually find someone who’s perfect for you. But for now, avoid the burnout. Take a break and just do your own thing. Then start dating in another month or few months. 🙂

  2. Hi! From what I’m reading, it seems like you get attached to them first. If you like someone and think they’re a great match, keep note of that but be aware of what actions they are showing you so you can understand the level of interest and not latch on too fast. Getting latched on too fast puts pressure on a relationship and can end it before it even has a chance to progress forward.

  3. If your assesment of yourself is accurate, and I am going to assume it is, I think you just got unlucky. Like others have said, these reasons appear to be outside of your control. Blaming yourself for things outside of your control is counter-productive.

    You mention approaching dating in an anxious state of mind. Do you think that might put guys off? Maybe guys misinterpret your anxiety as you not being comfortable around them, and then decide to eject? I personally would also feel like I didn’t « click » with a girl if she was tense whenever I’m around.

  4. Please don’t be hard on yourself. I’ve had friends who have had to cut things off with woman they began dating because they had so much to deal with in their personal life. You sound like a great person, and shouldn’t be too hard on yourself. Things will definitely turn around for you. Remember what you said, you’re quite a catch. You’ll find the lucky one to be in a relationship for sure.

  5. As someone who has been constantly rejected for the better part of 11 years, I can tell you, it gets easier to not care the longer you go without.

    Truth is if you are as great as you say you are, you are probably pulling hot dudes, or at least dudes with options. These are the ones everyone chases, they are also the ones who won’t settle, because of those said options. My guess is you didn’t put out (totally fine) as quickly as they wanted you to.

    They were probably holding on as long as possible, but sensed the « what are we » conversation coming, and knew that they didn’t want to commit.

    You are dating fuck boys. my sincerest apologies and I wish you the best

  6. Hi there, I (24F) was in your boat too! I was dating and on dating apps on and off for my entire adult life, and never found a decent partner or someone I felt a deep connection with. As I was planning to give up, I met an incredible and beautiful person online, who even lived 2 hours away, and he just moved in with me yesterday! It was a love I thought I could never find on an app, since it’s sooo hard on apps and especially during COVID. But, I took my time and didn’t force any connections I didn’t feel were special or would last. There were a lot of duds, and I was about to lose hope, but I know if I gave up my life now would be very different. Give yourself time between matches, date or focus on one guy at a time (which you may be doing?) and most importantly don’t force connection. Give something time to blossom and build that trust, and if it doesn’t then don’t waste your time. My personal philosophy is that after a while, if you feel you are uncertain about the other persons feelings for you, tell them you feelings up front, or ask them what they’re feeling! Be upfront! That way, there’s less room for anxiety and more room for confidence in you and the relationship.

    Also, on another note, you sound like a great girl! And I hope you find someone who sees that and is wowed by you as you are. Don’t let failed dates make YOU feel inadequate.

  7. Yup not every date you go on means relationship. Maybe either take a break or don’t focus so much on the « end goal » the less I’ve cared about being in a relationship the more the guy has wanted one with me. Also try complimenting him. It works every time.

  8. Instead of treating someone like the potential “one”, try dating inclusively until they actually are. This used to be common, but people normalized sex during dating, so, of course, it became more exclusive, serial exclusivity anyway, because people have less respect for dating than relationships only intended for longterm.

    Also, I’ve noticed dating exclusively either causes people to desperately cling to a bad relationship (anxious-attachment style) or toss a good one in hopes of greener pastures (avoidant-attachment). I can’t say stable(-attachers) don’t experience this, but inclusivity would give people a realistic view of the dating pool and I think it would give more guys a better odds in the dating sphere.

    If you choose to, then don’t hide the fact or it looks like you are cheating. In fact, I was cool with meeting his other love interests and wanted to see what he looked for.

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