Questions to Ask Yourself Before Heading Back into the Dating Pool

Single Girl Problems by Andrea Bain

Editor’s Note: The following is an excerpt from the book Single Girl Problems:  Why Being Single Isn’t a Problem to Be Solved.


Not only does the dating pool shrink as a woman gets older, but she may find herself competing with 20-somethings. A 55-year-old man, even one with thinning hair and a big belly, still has hopes of dating a smoking hot 25-year-old — and if he’s rich enough, it could happen. I don’t see a lot of successful 55-year-old women driving sports cars with men young enough to be their sons in the passenger seat. Maybe they want to or maybe they don’t, but the stigma and judgment about how mature single women should behave marginalizes them. Women are desexualized as they get older.

We all get more apprehensive about dating as we age. From the outside dating looks like a young woman’s game, and there may be a bit of truth to that, but older women have something young women don’t: they have their shit together. Older women know what they want, and they are not afraid to ask for it. I’m aware that there are a lot of women just like Carolina, who look good and feel good but who have trouble getting noticed, and naturally that has them asking “What am I doing wrong?” The answer is: nothing. Unless you are still holding on to past hurts, or you stop seeing yourself as a sexy, viable woman, you’re doing nothing wrong. Maybe you have convinced yourself that men your age only want to date young girls. Of course, that’s somewhat true, but not for every single man. Anyway, the older guy who is still chasing women half his age has a lot of issues. You don’t need that! Just remember: you are amazing, you can find love again, and any bad stuff that happened to you in the past is in the past. Try your best to leave it there and live the rest of your life.


  1. Hmmm! This sounds like an Interesting read. Singlehood, I feel is not a problem, and it is okay to wait, build and heal thyself, enjoy your life, and live with passion and joy. In fact, it is necessary, whether one is in a relationship or not.

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