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Dating in your thirties is a whole different ball game, with new truths and red flags that you just didn’t have to face when you were swiping right as a starry eyed twentysomething. One telltale sign he might be marriage material? He was, well, older. This filter worked pretty well back then, but once you cross that threshold into your third decade, and your dating pool is more exclusively men who are in their thirties and even early forties, you realize that age doesn’t mean much of anything when it comes to marriage readiness.

Sure, men in their thirties and forties are more established. They have less to prove, have friends who are married with kids, have careers, maybe even own a home, and probably have a few gray hairs. They seem primed to settle down. But how can you tell if an older guy is ready for forever or just dressed for the part?

Like all matters of the heart, it’s best to look past superficial signs and dig a little deeper. To help out any of you in this dating pool, I asked a group of thirtysomething single men what they think you should look out for in a marriage-minded guy. This is what they said.

01. Take a look at his past relationships.

This isn’t going to be one that you will likely be able to examine on date No. 1, but, according to Jack, discussing past relationships and your attitude toward marriage should be something that happens sooner rather than later.

Shane's advice? Find out if he ever had any serious relationships in the past and if he ever saw any of his past relationships leading toward marriage. "I think it's fair for a girl to ask why previous relationships haven't worked out," says Shane. "The response to those questions should provide an accurate glimpse as to his level of seriousness. If a guy hasn't approached his previous relationships with an openness towards marriage, it's unlikely he will change rapidly at the advent of a new girlfriend relationship." 

Dating timeline: To be safe, best to ask what a catch like him is doing still single by date two or three.  

02. Has he done the work since his last girlfriend?

Don't end the conversation after the past relationships talk. According to these men, it's also really important to know why it didn't work out. Or, perhaps more importantly, for him to know why it didn't lead to marriage. As Jack puts it, "If a guy claims that he wants to be married and he's dated tons of women . . . and he's never bothered to do the tough, introspective work to understand why he never committed (e.g., likely surrounding fear of commitment or consistently dating/chasing the 'wrong ones'), then that's a big red flag."

Jack goes on to explain, "To me, it's not about figuring out some set of criteria to know if a guy is/isn't marriage material, or if he does/doesn't have some issues (like fear of commitment) . . . it's more about discerning if he's been committed to changing and improving his dating life, or if he's in an endless cycle of bad dating habits that are unlikely to be broken when you date him." 

Isaac recommends asking the guy you're dating point blank what personal work he's done in the wake of past breakups. "Sure, he might say that he wants to pursue marriage, but you will find more clarity in asking him what has gone wrong with his previous relationships. What's different about him now that makes him think that things will be different in a new relationship?" 

Jack also advocates for uncovering a guy's progression. "A women would be wise to determine if the guy is simply doing the same thing over and over in his dating life, or if he's actually trying to change his patterns," explains Jack. "If he hasn't made intentional changes, you'll likely just be one more woman who wasn't quite 'the right one' when all is said and done. But if he has been doing that hard work, then I'd say there's some real hope."

Dating timeline: If this conversation hasn't already come up over dessert or a walk in the park, be sure to have this conversation before you make things exclusive. So let's say, as a general rule, by date number five.

03. Does he have a mature understanding of marriage?

Shane mentioned that it's important that a man demonstrate an openness toward marriage, which is good advice to be sure. But Chris adds that what often sets apart the man who is really ready for marriage from the man who just fancies he is, is a mature understanding of what marriage really means in the first place. The man who jokes about the ball and chain and someone to "keep him in line" is not likely going to be as eager to commit as the guy who sees marriage as an opportunity for growth and deep partnership. 

"I think most men deal less with of a lack of desire to commit and more with a lack of maturity about marriage," explains Chris. "You have guys that get very caught up in their lifestyle who want to commit but don't understand that commitment really means. All they see is a restriction of one's own freedom." Chris says, "Yeah, commitment does restrict your freedom in a lot of very superficial ways, but marriage is so much more than that, and mature men understand that this kind of commitment is actually very liberating." 

Dating timeline: This conversation should definitely come up after you and your guy have DTR’d (Defined the Relationship). If you are dating exclusively, what does that mean to him? If he hopes it might lead to marriage? What does that mean to him? If he can’t handle this conversation? There is your sign. 

Image Credit: Jess Hunter