My first relationship just ended. How can I expect to find someone else when it took 15 years to find her? | Leading questions

I’m nearly 30 and my first serious relationship just ended a month ago. It lasted eight months, she was my first girlfriend and first kiss, etc. She broke up with me in a very kind and respectful way, and I have been … OK, I guess.

The thing is, everyone has been saying to me, “But you must feel so much more confident now.” I don’t. My self-esteem and confidence wasn’t exactly soaring before I met her, but now I feel even less so. It just feels like most people are less tolerant or accepting of my shortcomings.

If this wonderful, understanding person couldn’t see me as worth it, or enough or whatever, how can I expect to find someone else when it took 15 years to find her?

Eleanor says: A person declining or ending a relationship with you is not a scorecard on your value. I know it sure feels like it.

But it’s really important to separate the pain of being rejected from the pain of being proven “not worth it”, because although they feel nearly identical, only one has actually happened.

People end relationships because of the relationship itself: they felt you were not a fit with them. The same trait that makes you not fit with one person can make you a perfect fit with someone else. And in the search for love, that’s what we’re really after: not approval, not having lots of people like us, nice though that would be. We want to find a relationship that fits. The fact this lovely person felt you didn’t quite fit together isn’t evidence of your objective value, any more than learning that your neighbour doesn’t like porridge would convince you that porridge is bad.

The bad news is, we can’t predict if or when we’ll find that fit. You asked: “How can I expect to find someone else when it took 15 years to find her?” and I can’t give you that. I can’t give you proof that you can expect to find someone else.

But do you need it? To stay open-hearted and optimistic, you need the hope, not the expectation, you’ll find someone.

It might feel daunting to do the things that would help you find someone new – putting yourself out there; giving new connections the benefit of the doubt – when you’re not even sure they’ll work. But nobody’s sure they’ll work. Hope can be the motivation where expectation can’t be. You don’t need to know that it’ll work out. You can be led by the possibility that it might.

In fact, that’s what everyone has to do in the search for love, no matter how many relationships they’ve had. Don’t think of yourself as unlucky in love, such that you alone have to subsist on hope when everyone else gets to dine on sumptuous certainty. A very long romantic history doesn’t get you across the line to knowing you’ll find a relationship, or even that the one you’re in will last. Everyone, no matter how historically well-liked or beautiful or charismatic, faces ineliminable uncertainty that can only be bridged by choosing to pay attention to the possibility that love might work out instead of the possibility that it won’t.

Remember, too, that self-esteem and esteem from others have to be separable if either is to last. You said you feel like “most people” are less accepting of your “shortcomings”. You might be right, but double-check to make sure it’s not you who’s withholding the acceptance you want. Often we feel things are happening relationally when in fact – or as well – they’re happening within us.

Other people’s love and acceptance is worth wanting – everybody wants to feel cherished. But try hard to separate uncertainty about whether you’ll find that with another person from whether you can feel it for yourself. Relationships are about finding a fit; self-esteem is about recognising worth. Neither one can replace the other.

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