The Washington Post

Ask Amy: Man questioning gigolo status should restart job search

DEAR AMY: Six months ago I met a beautiful woman who is quite wealthy. We hit it off immediately and began a wild sexual relationship.

I go to her huge home every day and spend the day in bed with her, as I lost my job last year and can’t seem to find another one.

She gives me hundreds of dollars in cash every week (which she calls “pocket change”), and I’m saving lots of money for my retirement. The problem is I’m feeling guilty about the whole situation, and I’m starting to feel like I’m being used.

She insists that she loves me. Should I end this relationship while I still have a little pride or should I keep taking her money until I have enough to buy a home and move to Florida? -- Confused

DEAR CONFUSED: Why is this woman giving you so much money? Is it because you won’t see her unless she pays you? Does she need to have power and control over you? Or is it because she loves you and is being generous?

If you don’t like being a gigolo, then stop acting like one. Before accepting the next weekly wad of cash, you should ask her what her motivation is.

If you are in a relationship with someone who loves you (and you don’t love her), and this doesn’t feel right, perhaps you should return the money, reclaim your pride and find another way to get yourself to Florida. If you are spending every day in bed with her, this would seriously impede your job search.

DEAR AMY: After a decade of trying to no avail to get my husband to participate in our marriage, I’ve decided to call it quits. The problem is that I am the breadwinner, and it would ruin us financially to split up.

We have a child in high school with some learning disabilities and social issues. I doubt she will be ready to fly the nest any time soon. I was advised by a family law attorney not to divorce for these reasons.

My husband and I are mostly friends but haven’t shared an intimate relationship on any level for 10 years. I stopped wearing my wedding ring and moved to another bedroom a few months ago. My plan is to remain married and living in the home but to go my own way.

How do I explain this change in our relationship to friends and family? I am at peace with this decision and, in fact, am feeling unstuck and hopeful for the future for the first time in many years. -- Looking Ahead

DEAR LOOKING AHEAD: Your friends and family (and your daughter) have probably noticed that you have stopped wearing your wedding ring. This gives you an opportunity to say that you and your husband are separating but have decided to continue to cohabit peacefully and co-parent your daughter.

A mediator or professional counselor could help you and your husband. But there is nothing to stop your husband from seeing a lawyer; he could also initiate a divorce, split up the household and ruin you financially. You should plan ahead.

DEAR AMY: “Loving Mom” wrote to you about her ex-husband, who is in and out of jail and recently violated their “no contact” court order by sending their young daughter a birthday card.

While your advice was compassionate, you made a mistake when you told this mother to notify the ex that he should contact only her (and not the child). If he contacts her, she is inviting him to violate this court order. -- Concerned Reader

DEAR READER: You are right. “Loving Mom” said her ex was not aware of the court order. I suggested that she notify him of the order and send him a copy.

You are correct that for him to contact her (as I suggested he should) would be in violation; better advice would have been for me to suggest that he only go through his (or her) lawyer if he wanted to be in touch with either the mother or the child. Thank you.

Amy’s column appears seven days a week at Write to Amy Dickinson at or Ask Amy, Chicago Tribune, TT500, 435 N. Michigan Ave., Chicago, Ill. 60611.

by the Chicago Tribune



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