"I would tell her how she was pretty and she would roll her eyes and say she wasn't," he recalls. "I would tell her she was a nice dresser and she would say she thought her clothes were frumpy."
"I thought I was saying all the right things, but I wasn't getting anywhere with Michelle," Rob adds.
Meanwhile, his friend Jeff seemed to have the women eating out of his hand. So Rob pulled Jeff to the side and begged him for help. Jeff's advice was simple: say things that sound like they're coming from your heart and head, not from a Tom Cruise film from the 1990s.
"So I dropped the 'you complete me' line," Rob said. "When I said things I really meant, I started getting places."
Sometimes, when talking romantically to women, it's not what you say but it's a matter of how you say it.
Keeping Jeff's advice in mind, here are seven things that a lot of women would like to hear:
"Would you like to..."
Fill in the blank. It could be about plans for the next date, or whether or not she wants red over white wine. This not only displays common courtesy, but also shows a woman that you respect her choices.
"Every day I find something else about you that I like."
This tells a woman that she is unique, that there are many good qualities about her and also conveys that the relationship is not getting stale.
"I've never met anyone like you..."
This is infinitely better than, "You remind me of my ex-wife, but in a good way." Women want to hear compliments, but stressing her individuality and uniqueness works better than comparing her to other women.
"Tell me about your day."
Yes, women like to talk and compartmentalise things. This is a good thing.
"I love the way you... sip your Chardonnay, fold your pyjamas, wiggle your toes, etc."
Again, women not only like to be made to feel like they have unique qualities, but that what they do is appealing, cute and sexy, especially to you. When you find one of those idiosyncrasies, let her know.
"Would you help me to..."
By nature, women are nurturers. If you ask one for help, whether it's picking a Mother's Day gift for your mum, or choosing a new rug for your living room, they are usually happy to step up to the challenge. This is not a show of weakness; it’s simply a way of saying that you would like her to be more of a part of your life.
"There is no one like you."
Are we getting the message that women like to be made to feel special and unique? If not, good luck falling back on the old standard: "Your place or mine?"