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Dear Annie: I’m a recent widow with an in-law problem. My late husband was a generous man and frequently lent money to his family, often without my knowledge. He did tell me a few months before passing away that he had lent his brother, “Simon,” several thousand dollars.

Simon has always been somewhat of a bully, not to mention a known thief and a poor money manager, but he promised to repay my husband after Simon received an expected work-related settlement. Simon can be somewhat intimidating to me (and to others), so I approached his sister to ask her advice about this since we became aware that Simon’s settlement had been received.

She offered to bring up the subject with him, and lo and behold, he exploded, saying that he didn’t owe me a thing because he borrowed the money from my husband, not from me, and since my husband died, he owes nothing to anyone! I know this makes no sense, but Simon has always “gotten away” with convoluted logic such as this. (I should add that his family has always tolerated and enabled his behavior.)

Are there any reasonable ways to address this? Or should I simply write off several thousand dollars that I do really need since losing my husband?

—Grieving and Not Prepared For a Confrontation

Dear Grieving and Not Prepared: I’m so sorry for the loss of your husband and now the stress you’re enduring all because Simon won’t keep his word. It’s reasonable to approach Simon one-on-one and simply ask him to hold up his end and repay the loan. The agreement may have been worked out between him and your late husband, but that money was likely shared between the two of you, as most things are in a marriage. If your husband were still alive, he would certainly want the money repaid to him, per their agreement, and if not to him, then to you.

If Simon cannot repay it all at once, discuss installments on a payment schedule that works for you. Depending on the amount of money and the state you live in, you could try pursuing the issue in a small claims court. If need be, it might be worth consulting a lawyer to see what legal recourse you have for recollecting the loan.

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Dear Annie: I’m engaged to an amazing man and love him dearly, but I get jealous when we’re with friends and other females show up. I have gone home early on a few of these occasions and trusted that he would make good decisions in these situations, especially because he knows that I’m a jealous person.

I don’t stay up all night waiting on him because I trust him, but it seems that once I go home, he has more fun and doesn’t make it home for another four hours or more, so how should that make me feel? I can’t wait to marry this man, and I want to feel like I don’t have a reason for my jealousy and insecurities. I just don’t know how to get there on my own.

—Bitter Bride to Be

Dear Bitter Bride: You’ve said it twice: You trust your fiance. It sounds like he’s given you no reason to doubt him in the past, and these continued, unfounded anxieties will only lead to a self-fulfilling prophecy. Perhaps he feels freer to enjoy himself and the company of these friends when you’re not there because he doesn’t have to worry what the “jealous person” in you might do in these social settings.

The good news is you don’t have to do the work and “get there” alone. Enlist the help of a therapist to work through these jealous tendencies and personal insecurities —and soon. They’d make for a terrible foundation on which to build your fast-approaching marriage.

“How Can I Forgive My Cheating Partner?” is out now! Annie Lane’s second anthology —featuring favorite columns on marriage, infidelity, communication and reconciliation —is available as a paperback and e-book. Visit http://www.creatorspublishing.com for more information. Send your questions for Annie Lane to dearannie@creators.com.