Dating Coach Kelsey Wonderlin on How to Tell a Man Is Ready to Commit

The Short Version: Women who work with dating coach Kelsey Wonderlin learn to spot when a man they’re interested in isn’t prepared to commit for the long haul. Asking point-blank “Are you emotionally available?” won’t necessarily get you a genuine answer, so Kelsey hands women tools, tips, and tricks that show how ready a man really is for a serious relationship.

Kelsey Wonderlin, a dating coach, has heard this story more times than she can count: the guy you’re seeing tells you one day that he wants a relationship, and the next day he says the opposite: “I’m not ready for a relationship.” Without any warning, the happily ever after you’d pictured falls apart.

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

Kelsey Wonderlin, a dating coach, teaches women to spot red and green flags starting on the very first date.

Kelsey teaches women to tell whether a potential partner is truly prepared for something long-term. Does looking good on paper make someone compatible? Does a first date that gives you butterflies mean they’re an emotionally safe pick? Women can work through questions like these in her two courses, “Attract Relationship Ready Men” and “Magnetic Dating Lab.”

Kelsey’s advice lets women finally date strategically, going in with insight and a few mantras that keep what they expect in check. With the right tools along, you really can find a match who’s ready for a relationship.

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

Reading His Emotional Availability on a First Date

According to Kelsey, you can get a sense of someone’s emotional availability as early as the first date. The trick is asking what she calls “weed-out” questions, the kind that sort first-date duds from possible long-term partners.

After you’ve gotten the basics out of the way (“What do you do for a living?” “Do you have any hobbies?”), you can move into more sensitive territory.

Kelsey told us that asking “What do you value?” can show whether your date is able to open up on a serious level. If a potential partner has trouble answering at all, you learn something about how self-aware he is, or isn’t. The question can also show whether he’s willing to learn more about himself.

“Asking questions based on core deal breakers for your identity, your worldview, your values, is really important,” Kelsey advised. Religion and politics, for instance, sit at the heart of a person’s values and often shape how they picture their future. A date whose views differ from yours may be giving you an early hint that you two aren’t compatible.

Kelsey builds women’s confidence.

Still, Kelsey said, if you’re comfortable, you can go deeper on a first date. She said two questions, “What does healthy communication look like to you?” and “How do you think trust is built in a relationship?”, can get at the heart of someone’s values. A careful, nuanced answer shows not just how invested a person is, but also their emotional intelligence.

It’s a potential red flag if your date reacts to one of your questions with anger or impatience, or, Kelsey said, answers a deep question with something shallow and surface-level. A surface-level reply isn’t necessarily bad in itself, but obvious disinterest in the question, or an outright refusal to go deeper, counts as a glaring red flag where emotional depth is concerned.

A green flag, by contrast, is a date who can talk about difficult experiences early 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. Being able to voice softer emotions, such as sadness, regret, disappointment, shame, or guilt, is a good sign.

Being emotionally available depends on being able to be vulnerable, which is exactly what weed-out questions invite. So if your date won’t or can’t answer them in a way that satisfies you, that may be a clear signal a serious relationship isn’t in the cards for them yet.

Strong Boundaries Make a Meaningful Relationship

Vulnerability is essential to building a serious relationship, but it matters just as much to balance it with realistic expectations and boundaries you set for yourself. You’d expect a man to honor your boundaries, so why not honor them yourself?

 “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 makes sense that so many of us let our emotions lead. After all, only one thing is more intoxicating than love, and that’s the promise of it! Still, Kelsey advises women to put healthy personal boundaries in place early in a relationship. If you’re falling for a first date before the check even hits the table, you could be headed for heartbreak.

Kelsey urges women to hold healthy boundaries with their significant others, and with themselves too.

That doesn’t mean you should bottle up or hide your feelings; quite the opposite. As Kelsey put it, your partner should be “attuned to their emotions rather than suppressing them,” and you should hold yourself to the same high standard. Still, letting your emotions run away with you isn’t smart either.

“Remember, you literally don’t know this person,” Kelsey said. Two or three dates aren’t enough to really know someone, and weed-out questions can only tell you 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,” she 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 suggested laying down a few specific boundaries at the start. If you’d rather text as little as possible before you meet in person for the first time, for example, say so plainly. “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.” 

How your date reacts to a boundary tells you a lot about his emotional maturity, and about how he’ll handle bigger boundaries later on, whether they’re financial, sexual, or about family.

Since nobody can read minds, it’s essential to say your boundaries out loud. “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.

Setting boundaries takes time, patience, and trust from both you and your partner, and Kelsey says those three qualities are something we only learn to reach over time.

Strategic Dating Helps Women Get to the Point

Anyone in a serious relationship will probably tell you the same thing: “Love takes time.” A whirlwind fairytale romance sounds tempting, but real life is rarely that magical, and genuine relationships need time to grow.

If you’ve endured more lackluster first dates than you care to admit, all with emotionally unavailable men, “it takes time” is probably the phrase you least want to hear. That’s why one of Kelsey’s key questions is, “Are you dating strategically?”

Kelsey teaches women to stay open-minded, set boundaries, communicate better, and put complex emotions into words.

Kelsey breaks strategic dating down into several parts. To start, know which qualities you want in a partner and what your non-negotiables are, while staying open to quirks and room for growth. Get ready for conflict resolution and put active effort into your communication skills. Perhaps most important of all, you need to be able to share what you feel in healthy, constructive ways.

“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. 

Knowing yourself, your values, and the type of partner you want before a new relationship starts can help you screen out emotionally unavailable men. The trouble is, the more men you screen out, the less hopeful you might feel about your own love life. Kelsey gets that, and she said the real secret to strategic dating is holding on to your 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.” Still, Kelsey offered encouragement to women who have yet to find “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.”

Strategic dating can help you separate emotionally unavailable boys from emotionally intelligent men, and set you up well to find “the one” for good.