Signs That a Man Is Ready for a Relationship – Advice From Dating Coach Kelsey Wonderlin

The Short Version: Dating coach Kelsey Wonderlin helps women identify when a potential partner isn’t ready for a long-term relationship. Outright asking “Are you emotionally available?” doesn’t guarantee an authentic response, which is why Kelsey gives women tips, tricks, and tools to help reveal just how ready a man is for a serious relationship. 

It’s a story dating coach Kelsey Wonderlin has heard time and time again: One day the guy you’re dating says he wants a relationship, but the next day he says something completely different: “I’m not ready for a relationship.” The happily ever after you’d envisioned is suddenly in pieces, and with no warning. 

“Nobody ever teaches us how to attract and sustain a healthy relationship. That’s why I do what I do,” Kelsey told us. 

Kelsey teaches women how to identify when a potential partner isn’t ready for a long-term relationship. If someone looks good on paper, does that make them compatible? If a first date leaves you with butterflies, are they an emotionally safe choice? Kelsey helps women answer these questions in her courses, “Attract Relationship Ready Men” and “Magnetic Dating Lab.” 

With Kelsey’s advice, women can finally date strategically, meaning with insight and mantras in mind to keep their own expectations in check. Finding a relationship-ready match is possible when you have the right tools in tow. 

“There’s a lot to learn here in order to get there, but it’s a learnable skill set,” Kelsey reassured us. 

Kelsey said it’s possible to glean a person’s emotional availability from the very first date. You just need to ask what she called “weed-out” questions — questions that can separate the first date duds from the potential long-term partners. 

Once you’ve covered the basics — “What do you do for a living?” “Do you have any hobbies?” — you can broach more sensitive topics. 

“What do you value?” is a question that can reveal your date’s ability to express himself on a serious level, Kelsey told us. And if a potential partner struggles to answer the question at all, then you have a better idea of his own self-awareness, or lack thereof. It can also reveal your date’s willingness to learn more about himself. 

“Asking questions based on core deal breakers for your identity, your worldview, your values, is really important,” Kelsey advised. Politics and religion, for example, are vital parts of one’s values. They often contribute to a person’s own vision for their future. If a date has viewpoints that diverge from yours, it could be an early indication that you’re not compatible. 

And still, Kelsey said, you can dig even deeper on a first date, if you feel comfortable. “What does healthy communication look like to you?” and “How do you think trust is built in a relationship?” are two questions that Kelsey said can get to the core of a person’s values. A thought-out and nuanced answer not only reveals a person’s investment, but their emotional intelligence. 

A potential red flag is when your date has an angry or impatient response to one of your questions. Or, Kelsey said, when they give a shallow, surface-level answer to a deep question. A surface-level response may not be a bad thing, per se, but a clear lack of interest in the question or a flat-out refusal to dig deeper is a glaring red flag in terms of emotional depth.

A green flag, on the other hand, is when your date can articulate difficult experiences early on in a relationship. “Somebody who, even on a second, maybe even a first date, depending on where the conversation goes, can share about things that have happened in their life that have been hard,” Kelsey explained. The ability to express softer emotions —  disappointment, sadness, regret, guilt, or shame — is a positive sign. 

Emotional availability hinges on the ability to be vulnerable. Weed-out questions encourage vulnerability, so if your date doesn’t or can’t answer the questions to your liking, it could be a clear sign that they aren’t ready for a serious relationship. 

Vulnerability is key to fostering a serious relationship, but balancing it out with realistic expectations and self-imposed boundaries is just as important. You’d expect a man to respect your boundaries, so why don’t you respect your own? 

 “A lot of my clients struggle with waiting until they’ve had enough time to really determine if somebody’s a good fit or healthy for them. They jump in and they get attached very quickly,” Kelsey told us. 

It’s understandable why so many of us lead with our emotions. After all, the only thing more intoxicating than love is the promise of love! But Kelsey advises women to set healthy personal boundaries early on in a relationship. If you find yourself falling for a first date even before the check arrives at the table, you may be setting yourself up for heartbreak.

This isn’t to say that you should suppress or hide your feelings — on the contrary. Your partner should be “attuned to their emotions rather than suppressing them,” as Kelsey said, and you should strive for the same high standards for yourself. But allowing your emotions to run away from you also isn’t wise. 

“Remember, you literally don’t know this person,” Kelsey said. Even two or three dates isn’t enough time to truly get to know someone. Even weed-out questions can only reveal so much. “What are they like when they’re stressed out or when they’re angry? What are they like in conflict with you? … You’re not going to know until it comes up,” Kelsey said. 

“Make this your new mantra: ‘What I know of him, I really like. And there’s so much more I need to know,’” Kelsey advised. She also recommended setting a few specific boundaries early on in a relationship. For example, if you’d rather keep texting to a minimum before your first in-person date, you should make that boundary clear. “Using your boundaries as a mechanism for revealing red flags is really important,” she added. 

“When you set boundaries or make your needs known earlier on, that person’s reaction to it is going to put their emotional regulation, maturity, and understanding — or lack thereof — on full display,” Kelsey continued. “You can let your boundaries be what I call red flag revealers. You can use them early to assess people’s responses to what you need.” 

Your date’s response to a boundary says a lot about his own emotional maturity — and how he’ll react to even more important boundaries down the line, whether financial, familial, or sexual. 

Voicing your boundaries is key, as no one is a mind reader. “Don’t jump to conclusions when your unspoken boundaries are not automatically respected. Establishing and respecting boundaries is only possible when both sides are communicative and in-tune with their emotions,” she said. 

It can take time, patience, and trust for both you and your partner to set boundaries, three qualities that Kelsey says we can only learn to achieve over time. 

Ask anyone in a serious relationship, and chances are they’d say the same thing: “Love takes time.” As enticing as a whirlwind fairytale romance may be, real life can be far from magical, and real relationships take time to develop. 

If you’ve been on more mediocre first dates with emotionally unavailable men than you’d like to admit, then “it takes time” may be the last thing you want to hear. This is why one of Kelsey’s core questions is, “Are you dating strategically?” 

Kelsey split the definition of strategic dating into multiple parts. First, you should know which qualities you’re looking for in a partner, as well as your non-negotiables, while still being open-minded to quirks and areas of growth. You should prepare yourself for conflict resolution and actively work on your communication skills. Perhaps most importantly, you should be able to express your emotions in a healthy, constructive way.  

“I always tell people, before you throw in the towel, really give strategic dating a chance and equip yourself with the information and skills that produce healthy, long-term relationships,” Kelsey advised. 

Entering a new relationship with a clear sense of who you are, what you value, and the kind of partner you’re looking for can help to weed out emotionally unavailable men. But the more men you weed out, the less hope you may have for your own love life. Kelsey understands this, and said that the real key to strategic dating is being able to keep the faith. 

“[Dating is] such an emotionally intimate experience that you’re going through with yourself,” Kelsey said. “While you’re in that place, it feels so hard and so permanent.” But Kelsey had encouraging words for women who haven’t yet found “the one.” “There’s nothing wrong with you if you haven’t found someone yet,” she said. “Your whole life can change in a couple of months when you meet the right person.” 

Dating strategically can help weed out the emotionally unavailable boys from the emotionally intelligent men, and put you in good stead to finding “the one” once and for all.