Ask Amy: A woman with wheels wants to pay for travel

Dear Amy: I have traveled to meet a wonderful man that I am really anxious to get to know better. I paid for the first trip to visit him.

He sent me a check for the upcoming second trip to visit him.

I am so excited to see him on this next trip, but I’m hesitant to cash the check.

I am leaning toward not cashing the check and just paying for this second trip on my own.

The check is from his and his wife's joint account, which they still share.

I am a very independent woman. I work hard and have been a very private person since my divorce 18 years ago.

I have no regrets in life, but feel if I cash this check, I will have one.

I have no drama in my life. I worry that this ex will make drama.

I do not need her in my business.

How can I express myself and return this check on my next visit?

– Stumped

Dear Stumped: Whenever your gut tells you to put the brakes on – even if you’re not sure why – you will be wise to pay attention.

Hard-working and independent adults pay for their own trips. Doing so puts you in the driver’s seat of your own life (making it much easier to apply those brakes, if it comes to that).

If you want to travel to see him, then do it!

When it comes to expressing yourself to Mr. Wonder Guy, try this as an ice breaker: “I’m curious: Why do you and your ex-wife maintain a joint checking account?”

If I were you, I’d wonder if this man is actually and officially divorced.

In the future, if you choose to accept money from him, you can let him know that there are many ways to offer reimbursement for an expense – aside from writing a personal check, which would expose your identity to the other account holder.

One way to even out this financial commitment would be for him to visit you, on his dime.

Dear Amy: I moved to a retirement community several years ago. A mixture of couples and singles live here.

Over time I’ve become assimilated into the community.

I’ve met someone who hasn’t been alone as long as I have. I met him in the major corridor of our complex. I put on my best smile and introduced myself. He is ruggedly handsome, walks with a confident swagger, and has a great and engaging personality.

I wondered why he didn’t seem to be attached to any of the attractive women who live here. He is popular with men and women, and I know there are other ladies here who would like his attention.

We have become close. We share many common interests. He is loving, tender, and considerate of my feelings and needs.

My problem is that I’ve fallen in love with him, however, I don’t want to be hurt if he doesn’t totally feel the way I do.

I’m afraid I might lose him! I’m afraid of being hurt.

I’d like your advice on whether I should break this off and take my emotional lumps now or stay and keep him happy.

– Senior Single

Dear Senior: My understanding about some retirement communities is that they can be hotbeds of … hot beds.

Your experience of meeting your guy in the hallway and perhaps being in competition with other women reminds me that attraction will always – to varying degrees – pull any of us right back to high school.

And, just like affairs earlier in your life, the feeling of love and attraction leads to extreme vulnerability.

You are afraid of losing him. You are afraid of being hurt.

I would venture that both of these things are inevitable, because as you age the reality of loss grows closer.

You should talk to this man about your relationship. What does he want, and what do you want? Does he want to be in an exclusive relationship? Do you?

I’d offer one correction: You ask whether you should “stay and keep him happy.”

You should only stay in the relationship as long as it keeps you happy.

Dear Amy: Is there a new or substitute writer for your column?

The replies have become noticeably less angry, newly apolitical, and actually helpful and kind.

– Bob

Dear Bob: I am the only writer for this column, which I have been writing for 20 years now.

Thank you for delivering one of the most backhanded compliments I've ever received.

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(You can email Amy Dickinson at askamy@amydickinson.com or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068. You can also follow her on Twitter @askingamy or Facebook.)