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7 Things You Should Know About Dating the Woman Who’s “Forever Alone”

If your new romantic interest has large gaps in her previous relationship history – what does that mean for the relationship you’re considering?
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There are a million possible comparisons to be made between the dating world and the job search world. Most of the time, people want someone who’s got experience – even if it’s not the most reasonable expectation. (Seriously though, why do you have to provide past work history for a self-proclaimed “entry level job?” It doesn’t make any sense. But I digress.)

When we translate that to our hunt for Ms. Right, there are bound to people who have continuous bad luck.

Sometimes, it’s a lack of properly applying themselves – such as, they’re pursuing women who obviously aren’t interested in them, or they aren’t pursuing any women at all – but sometimes these things come from a place of serious, perpetual loneliness.

In fact, there’s actually a dedicated subforum on Reddit for “forever alone women”. What do all these women have in common? Well, there’s no singular answer here – most people have different experiences when it comes to dating, and lumping anyone into a single, generalized category without understanding the reasons they choose to label themselves as such would be ethically wrong.

Instead, we would like to take a look at the common reasons why women have claimed that they are “forever alone”.


She may have self-confidence issues.

We all know that a woman with self-confidence is sexy, as long as it doesn’t border on arrogance. However, for many women, self-confidence simply isn’t something that comes naturally.

This can be particularly true for women with weight problems, acne troubles, eating disorders, or other perceived “bad appearances”.

There are a million different reasons why a woman could have self-esteem problems, and generally, they’re all hurdles in the way of having a successful relationship.

If you are dating someone who has previously identified as “forever alone” due to problems with her appearance, it’s of great importance that you help her to realize she is so much more than her perceived imperfections.

Of course, it’s also a good idea to reassure her that you think she’s beautiful just the way she is – but don’t take it too hard if she has a hard time believing you.

Admittedly, even for someone who has done my fair share of dating (no big gaps for me!), the struggles we face in regards to our image of ourselves can be nearly crippling.

It can be difficult to grasp the idea of someone new finding us attractive, because we don’t find ourselves attractive. But for the women who love us, this challenging task can be quite rewarding as they begin to see a new self-esteem emerge, and their lady begins to love herself as she is.


She may have depression or mental health issues.

Mental health is a serious problem that can be hard to understand if you don’t face them yourself. In fact, it’s nearly impossible for someone with no experience (whether firsthand or through education) to understand what goes on in the mind of someone with a mental illness.

The most common mental health problems facing those who identify as “forever alone” are depression, social anxiety, and eating disorders. (I know, I already mentioned eating disorders – but it’s important to note that it isn’t an explicitly self-confidence related issue.

Eating disorders are a serious mental health concern that has the possibility to take a life.)

If you’re dating a woman who has identified (or suspected) mental health problems, one of the most important things to note is that you most likely cannot actually help her.

I understand the urge to try and do so, and usually that’s not a bad idea as long as it’s coming from a place of love and understanding – but unless you are an experienced counseling professional, it’s unlikely that you can do anything to actually solve the problems.

That’s not to say that you can’t be there for your lady friend (whether platonic or not) in regards to her mental health needs. The larger her support system is, the more likely it will be that she can have a safe and happy recovery process.

But unless she is also soliciting the help from someone specially trained to handle her mental health problems, they’re not likely to get better on their own.


She may have recently come out or transitioned.

For transwomen and newly-out (or not-yet-out) women, the idea of dating can be overwhelming. After all, this is a time of learning about ourselves, and to add the complications of learning about someone else can add more frustration and stress. The woman may be scared or lonely, or a combination of the two.

I know that not everyone is attracted to transwomen (and likewise the transmen who still consider themselves a part of the lesbian community, too), and not everyone is interested in the idea of being a “learning experience” for someone. But from the perspective of these marginalized women, it can be heartbreaking to receive rejections on these grounds.

Imagine: You’ve finally got the courage to be real to yourself, to face all your fears and be honest – and someone tells you that you’re somehow excluded still. It would hurt, wouldn’t it? This is something that transmen and transwomen deal with on a regular basis – and newly-out or still-closeted lesbians face their fair share of it, too.

I’m not saying they should be treated as novelties, or that you should ask them out just to avoid being discriminatory, but if you are genuinely attracted to a woman – you shouldn’t let something as silly as her birth-sex or her previous romantic history keep you from pursuing it. Just make sure you’re being a good ally when you do.


She could be bisexual.

Something that’s always baffled me was that bisexual women are stigmatized as having twice as many potential partners, because they pursue both males and females, and the assumption is that they do so equally. However, the reality is that’s not often the case.

Many bisexual women are ostracized from both the lesbian community as well as the heterosexual community, leaving themselves nowhere else to turn but to other bisexuals – and even then, it’s not guaranteed. In fact, famous bisexual actress Megan Fox was quoted as saying she wouldn’t date another bisexual – only straight men and lesbians.

While she openly acknowledges the hypocrisy in that statement, her opinion isn’t that uncommon. Many lesbians will refuse to date a bisexual woman, strictly for the fact that she may have previously had sex with men and may again in the future. We may ignore the fact that most bisexuals are completely capable of monogamy, just as there are monosexuals who are incapable of remaining faithful. It all boils down to the person, not their preferences.

We’d like to think that it’s only the lesbian community that discriminates against bisexuals – after all, it’s one of the most popularized straight male fantasies to have a bisexual woman (or two) join them in bed. It’s the reason why “lesbian porn” is so popularized in the heterosexual community, and it contributes to some of the stigmas involving women and the implication of their sexual value. But, an unfortunate fact remains: Many straight men are also intimidated by the idea of having a bisexual girlfriend. This stems from the underlying myth that bisexual women are inherently less faithful.

If you’re interested in a woman, and her bisexuality brings to question the attraction you have for her, keep in mind that you’re likely not the only person to respond to her in that way. Of course, no one can impose equality on your preferences, but you may be limiting yourself and potentially ignoring the love of your life. (Hey, not every woman is the one – but you’ll never know if you don’t give her the chance.)


She could be submersed in her work/school/hobbies.

I understand that these can be three very separate implications, but sometimes, it’s not as important for a woman to pursue a relationship. In fact, it’s actually unhealthy psychologically to make the search for love your main focus in life. But sometimes, a woman who has dedicated a great deal of her time to being the best she can at something not-so-romantic may discover later that they missed out on a lot of opportunities, and choose to pursue romance.

In the cases of work and school being prioritized, these women are often successful and independent, making them great partners for someone else who is successful and independent. But that doesn’t mean that they’re automatically going to be good at being in a relationship, especially if they’ve never been involved with someone before.

For women who put their hobbies first, there is an assumption that these girls would be “nerdy”. But what’s so wrong with nerdy girls, anyway? They have passion and drive, they do the things they like, and they don’t let society dictate their interests. Sounds a lot like good girlfriend material, right?

If you’re interested in a woman who has been too busy to chase women in the past (or to allow anyone to enter her life), it’s important that you be patient with her. After all, entering the dating scene later in life can be really hard. This is true even without a slew of rejections. But if you reject her just because she focused on her non-romantic life first, you’re telling her that it’s too late – and we believe it’s never too late to find love.


She might just suck (as a partner).

Hey, there’s not always an explanation for why a woman could be perpetually single. There’s a chance that she’s just not a good partner, and she carries a reputation for it. In these cases, your hesitation to pursue may be completely warranted.

That doesn’t necessarily mean that it’s fair, though.

If this information seems conflicting, it’s important that you realize that a large part of the human growth process involves learning from our past mistakes and making changes in our life – and sometimes, bad past relationships make for better future relationships. This isn’t guaranteed, but it’s always an option.

If you specifically seek out a woman with a bad reputation “for the challenge”, you may be setting yourself up for failure – but in other situations, it’s entirely possible that the woman you’re chasing after has made fundamental changes in her life since her last partner, and the experiences of what doesn’t work in a relationship may have educated her on the finer points of romantic interaction. Again, it’s not guaranteed, but it’s not a miniscule possibility, either.


It could be something else entirely.

There’s no cut-and-dry list of reasons why some women aren’t successful in their relationships. Sometimes it’s them, sometimes it’s someone else – but it’s important to remember that it’s not always her fault.

If you’re thinking of asking a woman out, and the only reason why you’re not doing it is because she’s been single for a while – is it really that important to you? Give her a chance; you could be exactly the person she needed in her life to overcome her Forever Alone status.

Take care, and be good to each other!

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Author
Barbara is a 26-year-old lesbian living in California with her partner (and their “fur babies” - an adorably chubby puppy named Porkchop and a ball python named Ru). In the spare time she pretends to have, she enjoys horror movies, music of all varieties, reading, and complaining about the weather.

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