There’s a lot to say about Shaindy’s unrealistic expectations and her tendency to see the world in black-and-white. But first, I wanted to hear more about what she was doing when she wasn’t dating.

I asked her how she spent her time, and Shaindy told me that she was taking a sheitelmaching course and apprenticing at her aunt’s salon a few hours a day.

“Is that filling your time?”

“Not really.”

“What else would you want to do? Is there anything you’d want to learn?”

“Listen, we all know what happens when girls get degrees. It takes up loads of time and headspace and then how can they date? Plus, if you advance too much, you’ll intimidate the boys.”

“Hmmm. I beg to differ. But let’s put that on hold. Do you travel? Is there any country you’d like to see?”

“Are you trying to make me into a professional single or something?” Shaindy snapped back.

People seem to look at their single days as a holding pen, a place to pace restlessly while waiting for Prince Charming to whisk them away. What they also need to know is that marriage will not make you happy. It just multiplies whatever is already there. If you’re a calm, happy, person who likes yourself and knows that you have value and worth, then when you get married — very likely to another happy, confident person — you’ll both be even happier together.

But if you’re frustrated and miserable, marriage won’t miraculously change that.

“Picture two water bottles,” I told Shaindy. “If they can both stand on their own, great. But if one is nicked and needs the other to prop it up, it’s eventually going to collapse — and it may knock the other bottle down, too.

“You want to be able to stand tall on your own. If you spend your single days learning new things, volunteering, and doing enjoyable activities with friends, you’ll build yourself.”

Shaindy was quiet for a moment, then asked, “But if I’m really happy, will I give dating my all? Like, maybe I’ll be fine being single.”

“You can be happily single, even while very much wanting a husband,” I assured her. “I enjoyed traveling when I was single, but that didn’t mean I wasn’t still aching to be married. When I spent a three-day Yom Tov watching my younger siblings with their spouses and children, it was painful.

“But each stage of life offers different pluses and minuses. You can’t avoid the loneliness of being single, so you may as well enjoy the perks. Enjoy the freedom, the opportunity to learn new things and meet new people, the lack of financial burdens.”

“I guessss…..” Shaindy was clearly unconvinced.

“Shaindy, this is good practice for the rest of your life. We have this fantasy of getting married and spending the rest of our lives with our husband. But husbands daven three times a day, they learn two or three sedorim or work full- or part-time. They do errands and go to friends’ chasunahs and yeshivah dinners and generally aren’t around that much.

“If you’ve gotten good at filling your day in positive, productive ways, you’ll continue doing so even after you’re married. The more outlets you have, and the more you’ve developed yourself, the better a wife and mother you’ll be.”

I asked Shaindy to come to our next session with a list of at least five ways she could fill her time.

The next week, Shaindy read me her list: Take a makeup course so I can do more than just sheitels; start going to Mrs. Friedberg’s shiur; get together with my high school chevreh once a month; save up to visit my seminary roommate in L.A.

“I know that’s just four things, but I couldn’t think of anything else,” she said.

“That’s a fabulous starter list! You’re branching out professionally, spiritually, and socially. What about volunteering?”

“Not really my thing.”

“That may be why it’s perfect,” I replied. “We can work on our marriage while single. One way is by stretching our giving muscle, by doing the chasadim that don’t come naturally to us, by being mevater when we’re out with friends.

“I wouldn’t suggest doing something you’ll hate, but is there a chesed you can enjoy even as it stretches you?”

“Well, I have an artistic eye, and there’s this tzedakah organization that often asks for volunteers to help them set up their events. Maybe I could do that.”

“Sounds great! One more thing. I recommend you buy Shaar Habitachon, get a chavrusa, and learn it each day. If you’re single right now, it’s exactly where you’re meant to be.

“It’s too easy to look around and think that the only path to normality is to be engaged at nineteen — but the vast majority of girls are not married at nineteen. Stress and unhappiness fester in that gap between where my life is and where I think it should be. Try to fill it with bitachon instead.”

Shaindy slowly made the items on her list into reality. A month later, the volunteer coordinator where Shaindy helped set up events redt Shaindy to her great-nephew. Shaindy came to her first date a happier, more fulfilled person — but then new issues arose.

All coaching scenarios in this series are real; the characters are composites.

(Originally featured in Family First, Issue 927)