There is one big moment in every budding relationship that defines the next step. It can happen very early on (even when he is asking you out!) or a few dates in. But either way, it’s the moment when you decide: “boyfriend material” or “next!” In the hopes that good single men everywhere will learn from these love-altering experiences, here are some real-life moments that made women either want to go the distance or beg of him, “Hit the road, Jack!”

First, the deal-breakers:

1. The guy who made a bad call choosing his ringtone. There are some things a grown man might want to hide from his date early on — and a secret passion for boy bands might be one of them. “The biggest deal-breaker for me was when I called a guy and instead of hearing a ringing sound in my ear, he had arranged for an ’NSync song to play to callers,” says Eve, 27, a musician’s assistant in Los Angeles. “Changing his phone in the first place is so unattractive to me, but then it was such a cheesy song, too! I just said, ‘Forget it.’”

2. The man who acted immaturely at her landmark birthday party. “I had been on a few dates with a cute 22-year-old, so I invited him to my 30th birthday party,” says Jean, 32, a studio manager in Hollywood. “The party itself was great, but my date was so busy getting drunk as a skunk, he didn’t talk to me all night. An hour later, he got sick on the floor of the club, then stumbled off.” Instead of apologizing to her the next day, he got mad at Jean for not taking good enough care of him when he needed it. “That’s the present I got for my 30th birthday: grief!”
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3. The guy whose manners needed a refresher course. “I was set up on a blind date by my Spanish teacher,” says Louella, a 29-year-old baker in San Francisco. “The blind date asked me out, but when the bill came, the guy asked, ‘Do you want me to pay?’ I didn’t know what to say, so I said, ‘Ummm, I mean… we can split it if you want.’ So we did. Then, on the walk to my house, he lunged at my face and tried to make out with me. I can’t believe he asked about paying for dinner and didn’t ask about kissing me — it should have been the other way around!”

And now, the deal-sealers:

1. The man who nixed the three-day communication rule. Most guys are trained not to call too soon after a date. But sometimes, doing so can make all the difference. “Right after my first date with my boyfriend, he put me in a cab and said, ‘I’ll call you,’” remembers Jennifer, a 30-year-old magazine editor living in Manhattan. “I figured it would be three days before I heard from him — if ever. But five minutes later, my cell phone rang. It was him! He said, ‘Sorry, but I couldn’t wait. I just wanted to thank you for a lovely evening, and I hope we can do it again soon.’ I thought it showed such confidence and maturity.” Three years later, the couple’s still going strong.

2. The guy who stole her heart… but paid for her mustard. That’s what happened to Alexandra, 27, a photo assistant in Atlanta on her birthday. “My friend knew this cute guy, so I told her to bring him along for drinks. He felt bad for not bringing a gift, so I jokingly pointed to a tub of mustard on the bar and said, ‘You could get me that.’ The next morning, when I was taking my little birthday presents out of my bag, I found the tub of mustard at the bottom with a Post-it on it saying, ‘I bought this from the bartender for you!’ I’m a wacky, seize-the-moment kind of girl, so the spontaneous gesture was totally in line with who I am. I loved it. We went out on a date just two nights later.”

3. The man who empathized with her pain. “My father passed away a few years ago, and on Father’s Day, the man I had just started dating sent me a bouquet of roses,” says Lori, 32, a consultant in New Jersey. “I thought that was such a kind gesture. It was the perfect thing to take my mind off my loss — and get my mind onto something good.”

4. The man who presented her with a second-date surprise. “On my first blind date with this one guy, we had dinner and then went bar-hopping,” says 31-year-old Samantha, a grad student from San Francisco. “So when he asked me out again, I expected more of the same. Instead, he said, ‘I want to surprise you. I’ll pick you up at six.’ When he arrived, he was holding two grocery bags full of food, a bottle of wine, and some candles. He poured me a glass, lit the candles and made me the most amazing asparagus risotto I’ve ever had! I was totally impressed and knew instantly there was a lot more to him than I originally thought.” That was almost two years ago, and he’s been making her risotto (and paella, and chicken roulade…) ever since.

For the other side of the story, read Men’s deal-breakers (and deal-sealers).

Amy Spencer writes for Glamour, Real Simple, and New York magazine, among other publications, and is the author of Meeting Your Half-Orange: An Utterly Upbeat Guide to Using Dating Optimism to Find Your Perfect Match.


Article courtesy of Match.com.