Ask Amy: Advice for the Real World

DEAR AMY: We first met when I was 14 and he was 16, but when we reconnected we were both married to other people, and we left our spouses for each other. We were married for six years. This ended up being a very toxic and at times abusive relationship.

Then an old friend that I dated when I was 18 re-entered my life. I started an affair with him and haven’t looked back. My husband found out very quickly and we divorced.

My current lover was also in a relationship when we began our affair. I am 47 and he is 48.

He was/is dating a woman 16 years older than he is. She happens to have lots of disposable income. She is basically his “sugar mama.” He admits that he’s never been in love with her, but he respects her and feels guilty and obligated to her because of all the “gifts” she showers upon him.

My lover is a very attractive and charming divorced father of four. He doesn’t want a relationship unless it involves love and mutual respect. We have been dating for almost a year. His sugar mama knows about me but refuses to give up on the relationship. He promises me he wants to spend the rest of his life with me, but he continues to accept gifts and go on “dates” with her.

She has given him property, vehicles, clothes, trips, you name it. He swears that eventually he will end it, but he’s trying to figure out how to do it gracefully.

I am a smart, attractive, reasonably level-headed woman with a good job, and so far I have done OK supporting myself. The logical part of me says he will never leave her as long as she keeps showering him with what she substitutes for love, money, gifts, etc. I feel like this woman is preying on his vulnerability. He is a very soft-hearted guy and feels like his word is his bond. At one time he did promise her that he would never leave her.

I love him and don’t want to give him up, but am I playing a losing hand? — Lovesick in Texas

DEAR LOVESICK: My first piece of advice is that you should never attend a high school reunion. These high school hookups are not working out for you.

You seem to want to claim some relationship high road, but according to your own narrative, you have a habit of overlapping relationships, each marriage ended after you had already taken up with your next partner.

I suggest that you stop focusing on the “sugar baby,” and take a very hard look in the mirror. Your relationships do not reflect ethical choices or high self-esteem on your part. And, of course, you are with someone who doesn’t seem to value you very much.

It might be messy, but it wouldn’t be hard for him to end the other relationship. All he would need is a dump truck and the will to stop accepting gifts, along with the guts to offload the many gifts he has accepted under questionable and unethical pretense.

DEAR AMY: I am having trouble deciding whether to travel to an old friend’s birthday party. I haven’t seen this friend in nearly 20 years, but we have re-connected through social media. She’s renting a cabin for the weekend, asking for donations of money and food, and inviting several other friends from that time period to help celebrate. My problem is that I’m not sure how much effort to make on behalf of friendships that share only the past. This party would require me to take three days off work, drive 12 hours round trip, and contribute food, liquor, cash and a gift. How do I decide if it’s worth my effort? — Trouble Deciding

DEAR TROUBLE: The best way to push an old friendship into the “current” category is to spend face time with the person. However, my theory is that when people lead their account with a list of roadblocks (as you have done), they aren’t really motivated to personally connect. In your case the roadblocks are significant. You don’t sound eager to go, so send your best wishes.

DEAR AMY: “George’s Wife” complained about her husband’s lack of grooming on the weekends. You defended him! I wonder how he would feel if she stopped bathing, shaving, etc. whenever she felt like it. — Disgusted

DEAR DISGUSTED: Good point. Game on!

Contact Amy Dickinson via email: askamy@tribpub.com Follow her on Twitter @askingamy or like her on Facebook. Amy Dickinson’s memoir, “The Mighty Queens of Freeville: A Mother, a Daughter and the Town that Raised Them” (Hyperion), is available in bookstores.