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I like her, but I'm not sure I should carry on dating her


jonnyjojo90
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I'm a bit of a late bloomer being 31 and never been in a proper relationship (though I've had a bunch of casual / FWBs in the past). I've never been confident enough to attract the kind of women that I'd want anything long-term with.

Recently I've been on 3 dates with a woman who I originally met in college a couple years ago (we didnt properly speak until recently).

She is really pretty and has a nice personality too. We kissed a couple times and also texted quite a lot in between dates.

Not much else has happened and we're in no rush to sleep together.

But I feel a serious relationship might not work between us as we are very different in certain ways. Also I'm not sure I'm ready for one right now, I think my confidence is an issue and it feels too much to deal with along with everything else in my life.

At the same time I really enjoy her company and feel maybe I should just 'go with it' and see what happens. 

But I'm worried about hurting her in the event that I were to lose interest – how many dates is it acceptable to go on before realising she's not the one for me? I don't want to build her hopes up and then leave her heartbroken.

Edited by jonnyjojo90
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34 minutes ago, jonnyjojo90 said:

I've been on 3 dates with a woman who I originally met in college a couple years ago

This is exactly the 'play it by ear' stage. You get to know each other through in-person dates have fun and see if things are a fit for you or her. It's that simple. No need to wring your hands about the future or readiness or hurting her. Go with it and if it goes well great, if it fizzles, that's ok too.

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Being different in some ways is not necessarily a bad thing. You don't want to date your polar opposite, but also, you don't want to date your mirror image. Some differences are complimentary to each other.

That said, if you are seeing major deal breakers already, then it's best that you don't waste your time or hers on this. It all really depends on what you mean by seeing differences between you two and what they are.

If you are seriously looking for your one, then be careful about getting stuck with a place holder who is kind of OK, but also not good enough because that will burn precious time.

Be clear with yourself about what it is you are looking for exactly and what you are offering to that person that they should choose you. Keep in mind that relationships are a two way street.

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I see a lot of doubt.

- You don't feel certain you are 'ready' to be involved with anything significant at this time of your life?

- You are not sure if you two click.

- You don't feel you are confident enough to attract the kind of women you're really into? ( do you even know what that is?)

IMO, If you feel this just isn't for you, you speak up sooner than later and not lead someone on and on.  I am sure she will not be 'heartbroken', as it has only been 3 dates.. not 3 years.

I think someone dating does know if it's a true interest within 3 months time.  But, I do not agree with anyone faking it just to not hurt someone's feeling.

I've had guys walk away from any time of one month to five ( vice versa) .  And yes, I got over it okay.

If it's not there, then it's not there.

In the meantime, maybe consider working on yourself and figuring yourself out some more.. Maybe even considering working on your self confidence and/ or insecurities ( whatever's causing your problems).  And even consider NOT getting involved for a good while, as not to be in such a situation .

Never anything wrong with just being on your own to fix yourself, etc.  My brother went about 10 yrs after a long term fail and took his time.  He did end up meeting his wife after that time. 🙂 

 

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What are these differences?  I have a feeling you are looking for a reason to not be in a relationship.

  This lack of confidence puzzles me.  Most guys with low confidence don't get dates with pretty women or have several FWB over the years.  Specifically what part of you don't you have confidence about?

Lost

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1 hour ago, lostandhurt said:

What are these differences?  I have a feeling you are looking for a reason to not be in a relationship.

  This lack of confidence puzzles me.  Most guys with low confidence don't get dates with pretty women or have several FWB over the years.  Specifically what part of you don't you have confidence about?

Lost

Um, that’s not true at all. Low confidence in men doesn’t mean that we don’t sleep around at all. It just means we lower our standards, lol.

From your post it seems like your just over analyzing the situation. Your just dating so why put so much pressure on yourself to find out if she’s the one or not.

I’ve been in a similar spot before. What I’ve found is that no one is really perfect and oftentimes my standards are just too high for what’s available in the market or for what I can ask for.

My suggestion would be to date but keep your options open. If she isn’t the one, then that’s okay, and if she is then she is. It’s actually less about the person and more about you. 

The idea of there being perfect people, or houses or cars is silly. Sometimes it just depends on the type of relation we are able to build and foster with the people we interact with. Like the saying goes, one mans trash is another mans treasure.

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On 12/8/2021 at 10:17 AM, jonnyjojo90 said:

Also I'm not sure I'm ready for one right now, I think my confidence is an issue and it feels too much to deal with along with everything else in my life.

At the same time I really enjoy her company and feel maybe I should just 'go with it' and see what happens. 

But I'm worried about hurting her in the event that I were to lose interest – how many dates is it acceptable to go on before realising she's not the one for me? I don't want to build her hopes up and then leave her heartbroken.

What's going on in your life? Straighten that out before bringing someone new in. It's never a good idea dragging someone else into unfinished business or any issues you have unsettled. I think that may be affecting your confidence also overall. You'll feel better once you've got any ongoing issues resolved or at least have a plan in place to deal with them appropriately. 

From the sounds of things, it doesn't sound like this will work out but that's part of you not feeling ready or confident to start a new relationship with someone. 

If your heart isn't in this, don't proceed. You can still enjoy someone's company provided there are no misunderstandings about how available you are, mentally, emotionally, or you're both on the same page in terms of your involvement.

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I am of the thought, don't waste your or her time.

When you're into someone it's easy.  People waste time with a person they are unsure of for many reasons.  but the problem with that is, as you indicated, it can really hurt the other person. 

They see you calling, making dates, texting etc as continued/increasing interest and they invest more of themselves. 

Anyone that's looking for a proper relationship would rather be rejected, then strung along. 

Work on yourself. Your confidence. Don't play with people's hearts. 

You know whether or not this is  typical first dates uncertainty or you're just not that into her or it.

I tend to think it's the latter. the former should not weigh on your thoughts so much, when you're ready for a relationship and with someone you're romantically interested in.

 

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23 hours ago, junebug123 said:

Um, that’s not true at all. Low confidence in men doesn’t mean that we don’t sleep around at all. It just means we lower our standards, lol.

I would submit the opposite is true in that case.  People who feel they are "lowering their standards" obviously have a high opinion of themselves and therefore feel they are entitled to a certain level of person/partner, and thus a lower opinion of the many of those who do not meet this requirement.

To the OP -- having never been in a relationship before, possibly he has an unrealistic expectation of what a relationship actually is, and the other person's role in that?  Just a thought.

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While I think it's healthy to build different kinds and degrees of friendships and acquaintanceships that meet different needs, speaking only for myself, I get only ONE lover--at least at a time.

So for me, the term 'simpatico' means everything. That's someone who 'gets me'. Unless I feel THAT kind of click with a potential lover, then I'm not willing to participate beyond whichever date spells out for me--even if it's a first meeting--that I could never enjoy true simpatico with this person.

If you're comfortable being single, then you're not desperate enough to try to make mismatched puzzle pieces fit. You won't string anyone along, because you get that dating is not an obligation, it's voluntary, and it's THE time to get to know someone well enough to learn whether you're a great match--or not.

Allow bad matches to pass early.

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On 12/9/2021 at 12:42 PM, lostandhurt said:

I have a feeling you are looking for a reason to not be in a relationship.

Me too. What a self-defeating statement:

On 12/8/2021 at 1:17 PM, jonnyjojo90 said:

I've never been confident enough to attract the kind of women that I'd want anything long-term with.

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I’d also be curious about what the differences are. If your interest is high now, I don’t see why more dates would be out of the question. If you’re comfortable and get along great in person, and you enjoy her communication style during the in between then it sounds like a promising start.

I gave up on finding someone that’s exactly my mirror image or having all the same things in common ages ago. It’s more about the compatibility and comfort to where I don’t have to second guess anything. 
 

I too, wonder if you’re looking for reason to not get serious with this one. Only based off of what you posted and not having been in one before. Maybe she just doesn’t check all the boxes that you’re looking for exactly, which is fine, but could also be a long search to find someone perfect. Up to you, if your interest isn’t sky high after date three I’d wonder why and if there are dealbreakers that would make you think you’d eventually lose interest. 

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