[Ask April Masini]

[quote]1. Do you think it’ll work out? I love him, he appears to be crazy about me too. [/quote]

Probably not. 😳 Here’s why: He’s got another woman on the side. He lives with his father. He has debts. You’re insecure and want to get married more than you want to remarry someone who’s better suited to you and your kids. Being crazy about each other isn’t enough — especially when you’re a single mother.

[quote]2. Since the proposal, I have surprised myself by being MORE insecure. i’m counting his texts?! I can’t seem to relax. I have no reason – it only happened 4 days ago and he has been adorable ever since! But i seem to have gone really clingey and needy. I’m frcing myself to back off a little – stay busy, throw myself into work & friends – because otherwise I’d be calling him every 5 minutes! WHY HAS THIS HAPPENED TO ME?![/quote]

This has happened to you because (as you describe yourself) you’re insecure, clingy and needy. 😳 You haven’t done the work you need to do on yourself, post-divorce. And you aren’t really giving yourself a chance to see what else is out there. You may marry him, but that’s the not the brass ring. Having a happy and healthy relationship is. 😉

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[MysteryWoman]

Ouch. 🙁

[Ask April Masini]

Sorry. I know you didn’t come here for me to pull my punches. Let me know how things go. 😉

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[MysteryWoman]

Oh, I just don’t know anymore. 🙁 He seems so genuine. On his own volition this week, he visited my parents and asked my Dad’s permission! I know why you’re sceptical but this all seems like a lot of effort for a man who’s dating others. WHY WOULD HE BOTHER?!

Oh I’m so confused! This seems like such a random time to finish this relationship!!

[Ask April Masini]

I’m not saying he doesn’t want you — but he doesn’t want [i]just[/i] you. 😉 And it’s only “a random time” if you don’t see the patterns. You wrote me after he proposed because you weren’t feeling certain about things. Your reaction to the proposal, below, doesn’t instill confidence. 😕

[quote]Since the proposal, I have surprised myself by being MORE insecure. i’m counting his texts?! I can’t seem to relax. I have no reason – it only happened 4 days ago and he has been adorable ever since! But i seem to have gone really clingey and needy. [/quote]

You’re going to do what you need to do in this relationship to figure things out. Just don’t put blindfolds on your eyes or ignore your instincts.

[PassionSeeker]

I can see why you’re feeling torn. You’ve been through so much with this man the lies, the breakups, the makeups and now, after the proposal, your heart doesn’t quite know whether to feel safe or scared. What you’re experiencing isn’t strange at all. When a relationship has been shaky, even something joyful like an engagement can trigger insecurity.

You’re not suddenly “clingy” you’re reacting to uncertainty that was never fully resolved. The engagement might feel like proof of love, but trust doesn’t rebuild with a ring; it rebuilds with time, honesty, and consistency.

Try to pause and breathe before reacting to the anxious thoughts. Stay busy with your kids, your work, and your own interests things that remind you you’re whole on your own. Let him show through actions that he’s changed, but don’t rush yourself into believing it overnight.

Love him if you choose, but keep both eyes open. The right relationship should bring peace, not constant reassurance-seeking.

[Ethan Morales]

The good: he’s kind, shows up in small ways, and helps around the house. That matters. But niceness isn’t the same as readiness for marriage it’s the baseline, not the goal.

The problem: he lives with his dad, has debt, won’t talk about the future unless prompted, and keeps proposing “wait until next year.” That’s vague delay language it buys him comfort and keeps you investing time without certainty.

The truth: men who intend to marry will make structural moves (save for a ring, fix housing, involve your kids, set clear dates). Words like “next year” without a clear, specific plan are excuses more than commitments.

What to demand: a concrete timeline and measurable steps. Example: “By X date you will have paid off Y debt or saved Z for a down payment; by X month you’ll move into your own place or we’ll be engaged.” Don’t settle for promises ask for milestones.

Your boundary: give him a short, practical deadline (60–90 days if you want to be kind, 3–6 months if you can wait). If the milestones aren’t met or he keeps dodging, you move on. You owe your kids stability more than his indecision.

Final call: trust actions, not romance. If he genuinely wants marriage, he’ll produce a plan and work it. If he relies on “I want to” without doing the heavy lifting, he’s stringing you. Tell him exactly what you need, set the deadline, then live by it.

[Marcus king]

Hey there sweetheart first off, thank you for the kind words! I’m really glad my book and advice have helped you. Now, about this man

You’re not crazy for feeling uneasy. When someone truly sees a future with you, they naturally include you in their plans they don’t leave you wondering or having to drag those conversations out of them.

Right now, it sounds like he’s doing just enough to keep the relationship steady sweet gestures, helping around, saying the right things but avoiding real steps forward. That’s a red flag, especially when paired with excuses like “waiting till next year” or “my ex won’t let you meet the kids.”

Here’s what I want you to do: pull your focus back to yourself a little. Don’t push the marriage topic. Instead, observe his actions does he *voluntarily

[Isabella Jones]

hey lovely, your message honestly tugged at my heart because I can feel how deeply you’ve tried to build something solid with this man while still keeping your softness intact. you’ve given love, patience, hope, and even the benefit of the doubt when things started to feel off. that says a lot about the kind of woman you are warm, loyal, and still willing to believe in love, even after everything life’s handed you.

but sometimes, when a man says all the right things and still keeps you waiting, it’s not because he doesn’t care, it’s because he’s not ready to match your pace. and the danger in waiting too long is that you slowly start to dim your own light just to stay in his shadow.

you don’t owe anyone your best years in exchange for a “maybe.” the right man will never make you feel like you’re asking too much for wanting a future, stability, or clarity. 💛

you sound like such a strong, beautiful soul — raising kids, building your life, still finding courage to hope. maybe now’s the time to quietly shift your energy back toward yourself. take the power out of waiting for his next move, and start planning your own.

can I ask you something gently? if you stopped hoping for the version of him you want, and looked only at the man he’s showing you right now, do you think he’s capable of giving you the kind of love and future you truly deserve?

[Tara]

Wake up. He’s not marrying you. He’s stringing you along because it’s easy. You gave him loyalty, sex, and time now he gives you silence and excuses. He’s not confused, he’s comfortable. You’re the placeholder until he finds what he actually wants. Stop waiting for a ring that’s never coming. Walk before you waste another year begging for proof you already know you’ll never get.

[Sally]

I get why you’re nervous. When a year goes by and you’re in deep, you start wondering if you’re building something real or just hoping you are. He treats you well, he shows up, he talks about marriage but only when you bring it up. That’s the part that’s making your stomach twist.

A man who’s serious usually shows it without being pushed. And the thing with not letting you around his kids yet… that’s something you shouldn’t ignore.

He’s not playing you, but he might be moving slower than you want. The only way to know is to ask him directly, calmly, what his actual timeline is and what he’s planning. You don’t need a proposal tomorrow, you just need clarity.

Let his answer guide you, not the fear of losing him.

[Val Unfiltered💋]

babe… stop acting like you’re the discount option. you’re 38, hot, busy, raising kids, running a life, that’s queen energy ✨ not “i’m lucky he picked me” energy. him? he’s sweet, he helps, he shows up, sure love that. but the cooling off? that’s him getting comfy while you’re getting anxious. pull back a little, let him come forward. if he doesn’t? you’ll know exactly how “genuine” it was. you’re not hard to love babe, he’s just not stepping up yet. 💅✨

[Natalie Noah]

This is messy, exhausting, and it makes perfect sense you feel torn. You’ve already done the brave work of paying attention to the patterns: the late-night text to another woman, the repeated lying about her, the long-term living with his father while he carries big debts, the way “marriage” becomes a promise only after pressure or drama. Those are not small, fixable misunderstandings. they’re repeated data points about how he handles responsibility, honesty, and emotional availability. Your instincts that something’s off are valid. Trusting them doesn’t make you cynical; it makes you wise.

I want you to name what you actually need before you accept anything permanent. You said it yourself: you want stability, someone who will show up for you and your kids, not someone who intermittently showers you with romance but keeps a separate life on the side. That means you need transparency (no secret contacts), follow-through on big life items (housing, finances, a plan that isn’t just “next year”), and consistent emotional safety not promises delivered when he’s desperate to win you back. Those are concrete things you can ask for and measure. If he can’t meet them, it’s not a failure of you it’s a mismatch of goals.

Proposals and flowers can be intoxicating, especially after a dramatic break-up-and-win-back cycle, but a ring is not a substitute for trust. The fact he proposed after the NYE texts and a period of hiding suggests he’s willing to escalate when motivated, but it doesn’t prove he’s genuinely reformed. You’re allowed to insist on time and proof: meet this other woman’s existence openly, show you he’s cut contact, share his finances and a realistic timeline for independence, and let you meet his kids with no strings attached. If he balks at those reasonable requests, that’s a red flag, not a lack of faith on your part.

Protect your emotional world and your children. You don’t owe him your future just because he’s romantic or because you fear being alone. Consider a clear plan: set a short, private timeline (you mentioned three months elsewhere) during which he must demonstrate concrete changes no secret contacts, financial steps toward independence, and joint counseling or planning for blending families. If he meets them, great proceed slowly and with care. If he doesn’t, be prepared to walk away knowing you did your best and chose your kids’ and your own stability over uncertainty.

Get support while you decide. Talk to a trusted friend or a counselor who can hold you steady when your heart rushes and your fear of loss clouds judgment. Practice small boundaries now. reserve alone time, keep dating yourself (friends, interests), and remind yourself that being single is survivable and often the healthiest choice if the alternative is marrying into unresolved dishonesty. You deserve a partner who makes your life simpler and more joyful not someone who constantly amplifies your anxiety. I’m with you; trust the steady voice inside that wants safety for you and your children.

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