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Dating : I legitimately can’t allow my guard to go down. My overthinking/paranoia is going to ruin everything.

Dating : I legitimately can’t allow my guard to go down. My overthinking/paranoia is going to ruin everything.


Hi everyone!

I’m a 24 year old female. Some of you probably have seen my recent posts here. I don’t have the best dating history, I’ve been screwed over more times than I can count and I’m now extremely guarded.

Within the last week or so, I reconnected with a 27 year old male who I went to college with. He’s always tried to pursue something with me but we wanted different things at the time. He texted me this week asking me to just give him a chance after we had a brief conversation on Snapchat.

We went back and forth for TWO days about possibly trying something out. He lives two hours away right now and really it’s not ideal. He asked me to meet him halfway to grab dinner, which we did last night. We now text just about 24/7 some of its sexual but for the most part it isn’t.

We ate dinner and it was fine. Afterwards, we sat in my car for over two hours talking about everything. He explained how he’s 27 now and really just needs to get it together and settle down. He admitted he has feelings and such. I overthink things so I was skeptical of everything. He basically told me I’m in a huge emotional hole that I really need to start climbing out of because it’s just going to push people away. I brought up the idea that maybe he’s just putting on a front to get into my pants and honestly he wasn’t too happy that I said that and basically said if I wanted you for sex, I wouldn’t have driven over and hour for dinner and then sit here talking about a relationship with you for a couple hours. Overall the talk was good and now I just have thinking to do. Ultimately after hearing me ramble for over an hour he flat out asked me if I was even ready or could handle a relationship?

I really said I don’t know more than I could count. I’m pretty sure that’s all I could say. I told him I really just needed to think about things and seemed a little confused/disappointed because he was putting it all out on the table and the only thing I could say was “I don’t know”.

We did kiss, he played with my hair and kissed my forehead. It was all fine. He asked to see me again today but, I’m leaving for vacation tomorrow morning for a week so I needed to pack and so on. So I’m supposed to see him when I get back from my trip. He asked which part of Florida I’ll be in, which is Miami. He’s concerned I’ll find a guy in Florida and that Miami is completely unsafe (he’s a cop).

I’m constantly thinking everything he’s saying and doing are all a front but I have nothing to support that other than he was only into casual relationships in 2015, which I did also address yesterday.

How in the hell do I allow myself to chill the hell out without reading into or overthinking every single thing he does or says. I’m driving myself nuts and I really don’t know how long he’s going to remain patient with me.

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What do you think?

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  1. If you were transparently honest about where you’re coming from, I have to say that the ball is technically in his court about being patient with you, you know?

    As long as you’re openly communicating what you feel and how you’re feeling (especially when he looks you in the eye and asks) I really think he’ll not only understand but feel as though you’re trying. As a single, conscious bean myself, I understand that ominous cloud of doubt that storms through your has when things feel a little too… ”scripted” and ”perfect.”

    Secondly, I’m also at fault for doubting when a man tells me how he feels (both romantically and platonically). For me personally, I think it stems from my upbringing. I’ve witnessed my father say one thing to my stepmom and flirt with countless of other women, including my birth mother.

    -Please feel free to skip to the bottom for the conclusion and actual advice, lol-

    I know ”not all men are the same, ” but my personal guard is up. I’m not downing myself, but I’m humble about rating myself as a 6. I’m ”pretty/cute” but NOWHERE near ”hot/sexy.” So I’m the type the asks (in a romantic interest) ”why me?” I don’t like the idea that the person who’s interested in me also has 5 other interests at the same time. The worst thought (or scenario) is when he has a preference, but she isn’t paying as much of attention to him as he’d like so he ”pursues you” for the time being.

    Important note: I’m definitely not saying this is the case! I just wanted to share that you’re not alone with feeling this way and just wanted to give some examples from me personally.

    In conclusion! He sounds as though he genuinely cares and my advice for you would include looking inwardly. What do YOU want? Are you in a place where you feel as though a relationship would be beneficial or unnecessarily stressful?

    Second, ask yourself if you’re willing to put yourself in a position to be comfortable with being 100% opened. It wouldn’t be fair to any partner in a relationship for the other to keep them at an arm’s length without hope of getting closer.

    Dating and growing in a relationship should be something both parties are willing to work for. They should both feel safe to express their feelings and thoughts to one another and have confidence that even if their partner doesn’t agree, they’ll at least try to understand your thoughts and respect your opinion.

    I hope I was able to help in some way and wish you the best! ☺️

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