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Time to Decide About a Guy? Ask Yourself These Questions

There are two important questions that help women decide which man is right for them.
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Screenshot / Forsaking All Others / MGM 

“When it rains, it pours,” Anna, 28, sighed, beat and frustrated. She’d been enjoying the single life for a year or so—dating here and there, but it was all in good fun—nothing too serious. Then she ran into Charlie, and sparks flew like they never flew before.

That same week, she met Brian, and sparks flew just as high. It was as if she had won the lottery, twice. Both smart, both funny, and both genuinely good (and good-looking!), these two single men decided to enter her life at the same time. It was awesome . . . at first.

She wisely kept the ensuing dates light and casual, expecting that as time went on, it would become clear which guy was for real. But, to her surprise, no shining epiphany came. Instead, she found that both guys were for real, and she felt herself becoming closer to both of them. She soon learned that she could keep them at arm’s length for only so long.

Several weeks in, it was time to choose. Not only were conversations becoming harder to keep straight, but it was unfair to the men who were starting to talk about exclusivity, which sounded appealing—if only she could decide which one she wanted to be exclusive with. What normally would be a relief—an amazing guy who is ready to commit—felt like heart-wrenching torture when coming from two people.

Boohoo. Cry me a freaking river, already! you might be tempted to suggest. After all, to many women, this doesn’t sound like a dilemma—this sounds like a wonderful problem to have, like a scene straight out of a rom-com.

While the plight of women with too many suitors isn’t necessarily the worst problem to have in the world, it’s one problem that’s rarely given any sympathy. As I, too, can attest, it’s a painful decision. I once had to choose between a long-standing sort-of-more-than-friend who had finally decided to pursue something concrete and a handsome stranger I had met completely by chance at a concert. For weeks, my stomach was in knots, and my heart was torn.

So just ask the women who have been through this.

You may not be stuck between two men. But maybe you’re trying to decide what the future holds with one guy. In either situation, insight from women who have had to make a hard choice can come in handy when navigating the dating pool.

I spoke with eight women who’ve found themselves in a situation similar to Anna’s—choosing between two great men—before. As I analyzed the stories of Anna, Meghan, Kate, Michelle, Tracey, Claire, Anne, and Marie, I identified two important questions that helped these women decide which man was right for them.

01. Who is more attractive to me?

For each of these women, the question of attraction routinely came up—but it didn’t mean they were focused on looks. Marie put it like this: “Did one spend more money on me? Yes. Was he better-looking, objectively? Yes.” But that didn’t make her choose him—she ended up going with the other “objectively less handsome” guy. Because, to her, he was more attractive due to their compatibility.

“Sure, I went on a date with one man who really could be described as a ‘perfect candidate,’” Kate says. “Same religion, great job, handsome, really genuinely good guy. But I didn’t have the same level of attraction that I felt with the other guy.”

According to these women, their attraction boiled down to compatibility, not a checklist. But, knowing what feels compatible to you takes a deep understanding of yourself, as well as courage to follow through and go against convention. “Finding the right man is like shopping for a dress—the dresses that look great on the rack are not always the ones that fit the best,” Monica Gabriel told Verily readers.

While men are obviously much more nuanced and important than finding that perfect dress, I think it’s the ideal metaphor to describe compatibility. Knowing what kind of man works best with you comes from a deep sense of knowing who you are, which allows you to better follow your gut. And, often, it’s that pesky gut that knows what’s better for us than our brain. As Meghan shares, “I just knew he was a risk I’d have to take.”

02. Can I trust him?

“Trust is the glue of life,” writes Stephen Covey, author of the bestselling book The 7 Habits of Highly Effective People. “It’s the most essential ingredient in effective communication. It’s the foundational principle that holds all relationships.” I have found this wisdom to be true in the workplace, when buying cars, and even when writing relationship articles—and it was certainly true among the women who were deciding which man to date.

While the actual word trust wasn’t nearly as prolific in my discussions with these women as the word attraction, it’s clear that the women made their choices based upon whether they trusted one man over the other. This came up most often when the decision was between old rekindled flames vs. the new guy in town.

Take Tracey’s story. Her ex-boyfriend came back and decided he wanted to be with her, having broken up with her only months before. Of course, he did this at the exact same time she started dating another guy. “At first, I had lingering doubts . . . but I basically asked [my ex-boyfriend] point-blank if any of the issues we had previously would be gone, and he said he couldn’t guarantee it, so I decided [that it was] better to try something new than go back to what I had already done before.” Turns out that she made the right decision. Guy number two is now her husband and the father of her two children.

Michelle has a similar story. After dating her ex for five years, it didn’t seem like he was ever going to pop the question. “He had such a phobia about marriage, and it drove me nuts. He kept saying we could be together but not have to marry and have a title.” But because she did want marriage, she broke it off with him. A few weeks later, she started dating another man she knew from her childhood. After several months, her ex-boyfriend of five years found out, and begged that she come back and promised that he now wanted to get married. But according to Michelle, the trust was broken. The man she had only started dating a few months ago had already demonstrated far more reliability and dependability than the other guy had shown in five years.

. . . but what if you make the wrong decision?

When I had to choose between the longtime friend and the handsome stranger, I chose wrong. My mistake was that instead of trusting myself, I clung to an ideal of whom I thought I should be with—the man I had known longer. I instantly felt regret. Fortunately, I was forgiven by the man who mattered the most to me.

The women I spoke to all agreed that the right choice isn’t necessarily the man who gives the most compliments or matches a checklist or even the guy you’ve known longer.

Claire had decided to stop seeing the guy she was most attracted to because she felt like he wasn’t moving fast enough. “We had been on six dates together, and he still hadn’t kissed me,” Claire shared. “It’s funny because this is New York, and I was always complaining about things going too fast!” Convinced that his lack of physical affection was a bad omen, she decided to go with the guy who made his affections clearer, only to break up months later. But, like me, she got a second chance. “The six-date-still-no-kiss man came back, and, well, I just went on my seventh date with him.”

Anna, on the other hand, decided to choose neither of the men she was torn between. “Because I couldn’t make up my mind, I decided that it wasn’t fair to either of them to be with a girl who couldn’t decide between them,” she says. And while this was a hard decision, “an achingly hard decision,” in the end, she believes it was the right one. A month later, with her mind clearer, she found herself thinking more about Brian and reached out and told him as much. After they started seeing each other again, she began to realize that they had only grown in compatibility. “Having that time away from both of them really was able to give me the perspective I needed,” she shares. They’re still dating today.

The best advice we have? Know yourself, and throw out that checklist. No matter what decision you end up making, if you are humble and honest with your love interests, it will all work out in the end.