Something about this person worries me. How do I avoid ignoring red flags?

You need to feel safe with the person. If something is off, he advises checking it with a mentor rather than brushing it aside. Your gut, he says, does not lie to you: if something nags at you, or if you cannot be yourself around this person, it has to be sorted out now, not left for after the wedding.

“Your gut doesn't lie to you.”

She simply calls these worries concerns: even when everything checks out on paper, you may be troubled by his finances, her family background, the level of observance or a lack of attraction. That is not always a reason to run, but the decision will be better if you take the worry out of your head and onto paper: write the sentence I am concerned about continuing to date this person because, and finish it; then you can see whether it is serious or minor. Separately she warns about the cognitive dissonance of holding two thoughts at once, this relationship makes me miserable and but he is such a good person; such thoughts must be noticed, not drowned out. And a stop sign, she says, means literally stop: if you see one and have checked your perception with someone outside, you may have to accept that this person is not ready for marriage right now; the only exception is if he himself acknowledges his problems and shows a very clear commitment to growth.

“I'm concerned about continuing to date this person because...”

She puts the question bluntly: if you suspect the person is lying to you about something, first ask whether you are lying to yourself about how serious that problem is. The first deception worth exposing is your own minimising.

“Are you lying to yourself about the severity of the issue?”

A caution: a man had specific doubts; conversation with this partner did not flow, he felt no understanding and received constant criticism instead of acceptance. Three people he respected all answered the same way: everyone is nervous, you are too picky, you are not perfect yourself, and after the wedding, with the household and children, there will be no time to think about it. He listened, and it turned out to be their reality, not his: nothing changed, resentment toward the well-meaning advisers hid his spouse's good qualities from him, and the years passed in torment. Rav Pliskin adds an important correction: advisers see the couples who doubted and were later grateful, while the unhappy ones stay silent and do not come back to say it turned out otherwise.

“The feedback is usually more positive than the reality.”