Dear Anna,

I (31F) called off my engagement about a year ago and moved to a new city. A few months later I matched with a guy (26M) on an app — the second person I dated post-breakup. We hit it off immediately, but I wrote him off as relationship material: He’s five years younger, still finishing grad school, and had never had a serious girlfriend. I was six months out from my engagement and just wanted something casual anyway. So we agreed to keep it casual and became friends with benefits. For months we had a great rhythm: weekly hookups, hours of talking after, zero jealousy, real friendship. I told him about a health scare I’d been dealing with, and he was genuinely supportive.

Recently, after I was away for a few weeks, he asked me on an actual date — first time since we “broke up” from dating. He admitted he missed me, cared about me and wondered if we could work. I told him my real concern, that I want marriage and kids in the next few years, and I need a partner who’s stable and knows what he wants. He said he’s open to that life, but when I ask about his career goals, he shrugs and says he trusts it’ll work out. He also makes less than me, and I’ve been the one with more relationship experience — I’ve lived with partners before, been engaged. My friends, who’ve heard six months of stories about him, are rooting hard for us. My heart wants to try. My brain says hold out for someone more established. What do I do? Give him a trial run? Simply run? — Torn

Dear Torn,

Well. You already ran an experiment, of sorts. You’ve had six months of low-stakes friendship, presumably enjoyable sex, honesty and realness — that’s more real data than most people get from a dozen first dates. You know how he treats you when there’s nothing to prove. That’s rare, and it’s worth taking into consideration.

But your hesitation is worth taking seriously, too.

“I trust it’ll work out” isn’t a life plan. It's also not necessarily a red flag when you're 26 and still in grad school. I don’t think it’s realistic (or even fair) to demand that anyone in their 20s have their entire life mapped out.

So I wouldn’t ask the question, “Does this guy have his s— together yet?”

Instead, let’s try: Is he building the kind of life I could realistically build alongside?

And that’s something you can actually figure out.

Start with yourself. You already know you want marriage and kids in the next few years, but get more specific about what you mean when you say you want a “stable” partner. Do you want someone who earns as much or more than you do? Someone with a clear career trajectory? Someone who can reliably contribute financially if you fall on hard times? Someone who’s emotionally grounded and good at making decisions? Someone who can stay home with the kids or support you while you do? Someone who wants the same kind of family life on roughly the same timeline?

You may discover that what you’re calling “established” is really a desire for security — and that’s completely legit. (Though it’s not something any of us can guarantee. S— happens. People lose jobs, get sick, have to care of ailing parents and so on.) Or you may discover that you’re using career status and relationship experience as shorthand for qualities you actually care about more, a la ambition, responsibility, curiosity, follow-through and emotional maturity.

Now, look at him as he actually is, rather than as either your friends’ dream boyfriend or the underqualified 26-year-old your brain has constructed.

Is he curious about his future, even if he doesn’t know exactly what it looks like? Does he make thoughtful decisions? Does he take responsibility for himself? Is he a saver or a spender? Does he follow through on tasks? Can he talk about money, family, work and commitment without shutting down? When he says he wants a certain kind of life, does his behavior suggest he’s moving in that direction?

TLDR: He doesn’t need a five-year plan. He needs a direction and a will to walk toward it.

There’s one other thing on your list that I’d take seriously: He’s never had a serious relationship before. Again, that doesn’t mean he’s incapable of having one. Plenty of people have their first great relationship later than 26, and plenty of people with a long dating résumé are absolutely terrible partners. But it does mean there’s a category of information you simply don’t have yet. You haven’t seen how he handles sustained conflict, compromise, boredom, disappointment or the unsexy logistics of building a life with another person. That’s not a reason to reject him. It’s a reason not to assume that six months of being a wonderful FWB tells you everything you need to know about being his partner.

And there’s another question I’d ask yourself: If nothing about his level of career success or financial stability changed over the next five years, but he remained the same person you know and love now, would you still want this life with him?

Not because he’ll necessarily be the same person — of course he’ll change. (And so will you.) But because this question strips away the fantasy version of him you might be dating in your head. You can’t date someone’s potential. You can only date the person currently standing in front of you and decide whether you like the trajectory you’re seeing.

Which brings me to the trial run you mentioned. I say go for it. Give yourself permission to date him seriously for a while without deciding his entire future. (Or yours.)

Go on actual dates. Talk about marriage and children. Talk about money. Talk about where you each want to live. Talk about what partnership means to each of you. Go on a road trip — my favorite litmus test for compatibility. See what happens when the relationship has actual stakes and isn’t protected by the casual arrangement you built around it.

And then pay attention to how you feel. Do you feel like you’re constantly waiting for him to become someone else? Or do you feel excited about building something with the person he is now?

Because I suspect your real choice isn’t between your heart and your brain. It’s between loving who he is and betting on who you hope he’ll become.

Goals are worthwhile and wonderful, and so is ambition, but it’s not the be-all and end-all of what makes someone a good partner. If he doesn’t have the whole map but he’s headed in the same direction, I’d be willing to see where the road goes.

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