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Am I being a fool by allowing myself to be optimistic?


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Hi all,

Apologies if this is the wrong place to post this - I'm new here!

At the start of this year, I was dating someone for a few months. For perspective, I'm 29, male, she's 29, female, we both are single parents. After a few months, things were actually going really well, we were having a really nice time together, but she expressed concerns that she wasn't feeling as excited about the future as she felt she should be at the point we were at. She did express that she felt that this might have been some kind of self-sabotage because she did feel incredibly happy around me, and she couldn't find a justifiable reason for not being excited about the future. I also found it a bit odd that after just two months she found this to be the case as she'd insisted on a number of occasions that she was a "slow burner". But if she wasn't feeling it, she wasn't feeling it and I understood this. It also didn't help that her usual sitters; her grandparents had been away for a long time so we hadn't really been able to do anything date-wise, because we had to have her 11 year old with us every time we saw one another. This was 100% fine with me, but I know that she'd have liked some 1 to 1 time between us outside of being passed her daughters bed time - things like going out to the movies, for dinner, etc. 

This was a shame, as I had spent a lot of time with her and her 11 year old daughter and become rather attached to both of them, but I did understand, and from there, we went our separate ways and did not speak. This was around the start of March I think. 

Anyway, I was feeling rather low a week or so ago, so I decided to message her. Just to ask how she'd been doing. She replied that she'd actually been thinking about me on her way into work that morning and sent me a long message about how her and her daughter had been doing. A few hours later, and we'd established that we both missed one another, that she'd wanted to send me messages on a few occasions but "didn't want to mess" me about, and that I'd also wanted to on several occasions but wanted to give her space. 

So here's where we're at now:

We've agreed to meet up for coffee at her house (when she's back home - she's currently away on holiday with family). She's told me that she's still the same indecisive person so she doesn't know what she wants from this (I honestly wasn't expecting her to want anything so it took me a little by surprise when she divulged this information), but that she would find it odd not being affectionate with me, odd being friends as we've not done that before and that she "will probably want more". 

She asked me what I wanted from the situation and I'm a 100% honest person so I told her that whilst I had zero expectations (this is very true, I'm expecting nothing here), I still wanted to be with her. 

We've been talking every day since - frequently before she went away, and even whilst she's been abroad, we've been messaging once per day just to check in (she told me she wanted to do this - I was going to leave her to enjoy her time away). 

So I guess, the reason I'm here is, am I foolish for being optimistic about this connection? I wasn't, when we first started talking again. However, with every little bit of extra information she tells me (she's told me some very intimate information regarding herself, her daughter, and her best friend), I find myself getting slightly more optimistic. Which is giving me hope. Which is setting myself up to get hurt, potentially. 

Any input/advice, would be much appreciated. 

Thanks for reading <3

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I wouldnt say "a fool". She gave you a hint that she might want to get back together so you are optimistic about it. There is generally nothing wrong about that.

But, you also need to consider a following: An indecisive person who doesnt know what she wants, would think of something one day and something else the other day. Meaning that one day you would be her favorite person ever. And the next day she would discard you like you are nothing saying how she "doesnt feel it" or whatever other excuse she uses. So dating somebody like that isnt really reliable if your goal is a healthy long-term relationship. So if you want to get back with her, you need to be aware of that and take it into consideration.

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Know your worth.  Do not give this person the privilege of your friendship and affection while she is "confused"(but not so confused that she doesn't know she still wants the benefits of acting like a couple when it suits her).  Tell her - I want to be with someone who is reasonably sure they see potential for a future and don't feel confused.  I have enough friends and I'm not up for casual dating with you.  So if you find yourself feeling sure that you see a future here and you want to date me with that in mind you can contact me and if I'm still interested and available I'll consider it.

(And please stop letting her daughter get attached to you -she's at such a vulnerable age! kids don't "get" dating -they "get" attached).

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