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Why is dating so hard? Here’s what you said.

(Lettering by Olga Vasik for The Lily)

This article was originally published in the Lily.

Some people enjoy dating. I am not among them.

Before I met my partner, an unfortunate series of dates left me fatigued.

There was the soft-spoken high school teacher. Over a candlelit dinner, he revealed that he was preparing to divorce and was very sad that someone had stolen a backpack his wife had given him.

There was the techie. On date two, he dropped a pop quiz: How many dates would it take me to sleep with him? (a) 0-2, (b) 2-4, (c) 4-6, (d) six or more. If the answer were six or more, he stated gravely, I’d be doing myself a disservice.

There was the slightly older man. I’ve forgotten his occupation but not his insistence: He badgered me to come up to his apartment and fumed for the rest of the evening when I said no.

When I reflect on my younger years, I realize that I was dating while ignoring my instincts. That didn’t excuse some men’s bad behavior, but it did explain why, after dismissing small signs that gave me pause, I encountered larger issues that left me deeply disappointed.

The search for companionship can be complicated by any number of factors — emotional blind spots, mental health, a fast-paced career, family obligations.

The Lily’s launching a new series, “Dating While _________.” Several of you filled in the blank, telling us about the circumstances that affect your dating life.

Finding a person — or people — with whom we fit requires work, as does maintaining a relationship. But when you land a good one, the rewards can be rich.

Responses have been lightly edited for clarity.

“A successful date will give me a rush which lasts almost long enough to get to the next one without experiencing low mood. I am constantly looking for my next mood lifter, and worry constantly that things will go wrong and I will have many days of very low mood afterward. I’ve had early-stage relationships which have ended because I’ve told them about my illness or they have found out due to a chronic attack. I’m also wary of dating because I know I measure my self-worth in whether a man is paying me attention, despite being a feminist.”

“I currently live with my parents. My family is very close-knit, so to date me is to spend a lot of time with all of them. It can be difficult. I’ve obviously outgrown a curfew, but I do try to be courteous to everyone I share a space with. It also means that I have to go out more, or spend time at my boyfriend’s place, because my home is a shared place.”

“I’ll only date men who were married and have children. Also, I’m a widow (for over eight years) and some men have hesitated as they think I may have emotional issues due to the loss of my husband. It’s hard to find an eligible man who was married, has kids and can write a full sentence with correct punctuation and grammar.”

“You’d think the options would increase while bi, but I think there’s an additional hurdle where there’s a binary of either you’re gay or lesbian, and you have to ‘choose’ a side. I do explain it to potential partners — that occasionally brings out insecurities and distrust. My friend once made a joke that identifying as bi means everyone thinks I want to have sex with them, but hey, we have standards, too.”

“Not only is dating while an attorney difficult, but there is added difficulty when both I and my partner know that I care about my career in a way that we typically see of men. It’s not just the late hours and the weekends full of work, but it’s the fact that I expect my boyfriend to ‘be the wife.’ To be the primary caretaker of our future children (should we have any), to take on far more of the domestic duties in the household, to make sacrifices so that I’m well rested and can crush it at work. Of course, this can come with a plethora of difficulties when a cisgender female is dating a cisgender male. Not only is it about a reversal of heteronormative gender roles, but it’s also an issue of balancing work and time off with someone who has a far less demanding schedule and who is always sacrificing for you but to whom you can give far less time and attention. The circumstances have had an impact on how often I’ll go out on dates, and certainly who I’ll date.”

“One of the biggest things that affects my dating life is my separation anxiety due to my upbringing. I grew up in and out of foster care, and it just felt like I never had anyone constant in my life. It’s been hard for me to date because I get attached so easily, and in return I feel like that scares people away. When someone does leave, which seems to be inevitable in my life, I feel as though I take it harder than most. Because of this internal mental struggle, I am always hesitant to tell my dating partners, but I feel like they should know. I feel that it causes dread in my relationships because I always feel they are going to leave, and if they do, how will I recover?”

“I’m a fat, polyamorous, bisexual woman with mental illnesses, and that complicates everything so much, from finding a partner to keeping them and your own mental health. Living in a country as conservative as India doesn’t make dating any easier either. … I know my existence is subversive, but it’s almost as if nobody is willing to accept all of me as I am, and wants me to shrink (literally, and metaphorically) to fit the convention of normal.”

“I decided to start a family on my own and become a single mom by choice. Two-and-a-half years ago, I started fostering children. Since then, I’ve fostered seven infants and toddlers, and I’m finalizing the adoption of my 20-month-old son, Jack, whom I’ve had since he was 3 months old, and his newborn brother, Henry. Dating as a single mom with a toddler, a newborn and a demanding career means I hardly have any time or energy to devote toward men, and my two children either scare them off or intimidate them — they think since I have my own home, career and children, there’s no room or need for them.”


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