The Bad Date Diaries

Copyright © 2023 Jilly du Plessis All rights reserved. No part of this book may be reproduced, stored in a retrieval system, or transmitted in any form without permission in writing from the author. While this book is inspired by and loosely based on real experiences with online dating, it is a work of fiction. Timelines and incidents have been altered, and names and identifying characteristics of individuals have been changed. Businesses and places are products of the author’s imagination. Edited by Giovanni Jacobs This book is dedicated to my cousin, Tamaryn, whose hilarious foray into the world of online dating inspired much of this book. Contents Chapter 1 Chapter 2 Chapter 3 Chapter 4 Chapter 5 Chapter 6 Chapter 7 Chapter 8 Chapter 9 Chapter 10 Chapter 11 Chapter 12 Chapter 13 Chapter 14 Chapter 15 Chapter 16 Chapter 17 Chapter 18 Chapter 19 Chapter 20 Chapter 21 Chapter 22 Epilogue Chapter 1 MY OVARIES are about to shrivel up and die. At least, according to my mum they are. Apparently, that’s what happens when you turn thirty. I love her dearly but the woman is a bit of a drama queen. I’ve just endured a thirty-minute telephone call from her asking if I’m still single and listing all the reasons why I need to settle down and start a family, not least of which is the state of my ovaries. I think her exact words were, “Catherine, you know it’s all downhill once you turn thirty? Declining fertility. I read all about it. Your ovaries are going to shrivel up like prunes. There’s no time for faffing about, darling. We need to find you a husband.” Wouldn’t she be surprised to know that I’m currently rushing around like a madman because her phone call has made me late for a blind date? Surprised is not the right word. Horrified is a more accurate term. I was a bit appalled myself when my cousin Clementine suggested online dating. “Where is it?” I mutter to myself, as I fly around the room trying to find the black dress that I had in my hands a few minutes ago. I rifle through the piles of discarded dresses that are sprawled all over the bed. “Yes!” I give myself a mental fist pump as I locate the dress and scramble to get it on. I hate being late. I also hate the mess, but there’s no time to tend to both, and being punctual matters far more right now. The problem with being an only child is that there is all this pressure on you to settle down and procreate. Especially when you’re from a well-to-do family where words like “legacy” and “heritage” are frequently thrown around. During the call, my mother also informed me that her death is imminent because she is so very old (she’s not) and if I really loved her, I’d give her a grandchild who is sure to keep her mind young and healthy. She also read an article saying that grandparents who babysit their grandchildren regularly are less likely to develop Alzheimer’s. I’m not sure how that will work exactly when she lives in England and I’ve just moved to America, but in true Felicity Callahan style, she wasn’t about to be bogged down with the details while delivering her speech. While my dramatic mum might induce some eye-rolling, the truth is that since I turned twenty-nine last week, I really have been feeling a bit like an old maid. Thirty is fast approaching and I'm nowhere near settling down. I thought at the very least I’d be married by thirty. Instead, I’ve spent the last ten years building a career I’m proud of. I’ve had some short-term, casual relationships here and there, and one more serious relationship that ended in disaster. When friends ask if I’m single I always joke, “I prefer independently owned and operated”. I haven’t really felt that I needed a man. Until recently, that is. After things ended with Johnny, I was content single. But these days I look at Clem and her husband, Dan, and their twins, and I feel pangs of benign jealousy because I also want that. I want a man who will look at me the way Dan looks at Clem. I want a family. I’m too young for a mid-life crisis. Is there such a thing as a quarter-life crisis? I think I’m having one. It must be because, in spite of feeling the pressing need to settle down, it’s the only reason I’d agree to something as crazy as online dating. I like order and control, and doing something like online dating is way, way out of my comfort zone. I’d told Clementine it was a bad idea, but she reassured me that it’s dating in the 21st century and it would help me to loosen up a bit. Where else was I going to meet a man? As Clem had gently pointed out, I spend most of my time working and there are no eligible bachelors at work. This is true. Aside from one fresh-faced co-worker named Todd, who’s way too young for me, the only men at work are either old, married, or gay. Or all of the above, and considering I’ve only been living in America for five weeks, these are really the only men I’ve spent any time with. “Was that Lady Floss on the phone?” Clem asks as she appears at the door of her guest bedroom, which is where I’m currently staying until I find my own place. My mum doesn’t really have the title of Lady, but she comes from a long line of British aristocrats and certainly behaves as if she is part of the Peerage. Her snooty ancestors are probably rolling in their graves at the knowledge that she married an Irishman! That thought always gives me a little chuckle. Thankfully, she also has a great sense of humor so when shameless Clem calls her “Lady