Family Encyclopedia >> Family

Rediscovering Dating as a Single Mom: Navigating the Challenges and Realities

As a happily single mom, I'm not quite ready to dive back into dating or relationships. Not yet, anyway. Preparation is key to success, so let's refresh on dating basics and address the infamous 'suffering of dating.'

From flirtatious glances and subtle phone number exchanges to the dates themselves—I thought my days of this were behind me after years in long-term relationships. But life has a way of surprising us. While I'm in no rush, that chapter may return. To ease the transition, here's my preparatory guide to dating. Single ladies, chime in! Tips are always welcome. 😉

Table of contents

How do you find that nice guy?

Finding the right man for dating seems straightforward, but it's not always. I believe in letting him pursue you—think of it as the classic 'hunter' dynamic. If he's truly interested, he'll put in the effort. Don't chase; a little 'hard to get' can spark healthy competition and investment from him. (Unless casual fun is your goal, in which case options abound! 😉)

Search 'dating' on Google, and you'll discover countless apps and sites, from general platforms like Tinder (who dates without it?) to niche ones for highly educated singles. Is that discriminatory? Maybe. Personally, I'd love a chance encounter at a pub, grocery store, or even on a white horse—vintage dating at its finest.

Who is suitable?

Dating is personal: Who fits your vibe for drinks or dinner? You might picture your ideal type, but I've learned looks fade in importance. Prioritize humor—we all need someone to laugh with. Tattoos might make me swoon (superficially, I admit), but they're not deal-makers.

Read also: Tattoos and prejudice

Seek a thoughtful man who opens doors, listens genuinely, and shows interest in your life. Bonus if he's attractive!

What are we going to do and where?

Dates blend excitement and nerves. Opt for activities to ease tension—a drink is low-pressure, letting you gauge interest and control the evening's length (a little alcohol helps relax, too). Dinner works if vibes are good but can drag if not. Skip home dates initially; public spots feel safer, especially with blind dates—you never know.

Read also: dating tips for single moms

Finally, some points of attention about the suffering of dating

  • Enjoyed the meal? Offer to split the bill politely. If he insists, graciously accept and thank him.
  • Dress for the occasion—no heels for laser tag!
  • Eat normally; men appreciate a woman who enjoys her food without pretense.
  • For relationship goals, hold off on sex—rushing can send mixed signals and lower long-term chances.
  • Avoid stalking texts; if he felt the spark, he'll reach out. Desperation isn't attractive.
  • You can always leave if it doesn't feel right—your comfort first.
  • Have your own transportation.
  • Trust your intuition; that first gut feeling is often spot-on. 😉

Photo used via Shutterstock