Resume dating, but slowly

Dear Amy: I am in my mid-50s and have been married four times. I am a recovering alcoholic and drug addict.

I abused substances for 35 years. I have been clean for three years now and my life today is beyond my wildest dreams. I have repaired the relationships in my life with family and have built solid friendships today with people I have met in recovery and at work.

I have done a lot of work on myself, with the help of therapy and AA. I believe I am the best version of myself today, however I am concerned with people judging me by my past life.

How do I start dating and explain four divorces? Who would want to take a chance with a guy with such a turbulent past life? Do I bring this up on a first date? Do I wait to be asked?

Stormy Past

Dear Stormy: Congratulations on your continuing recovery. It is truly inspiring.

You’ve already persuaded four women to put their trust in you, over the years. Now you just have to figure out how to do it, sober.

The way to date is to start doing it! Tiptoe into the shallow end of the dating pool, with the help and support of your sponsor and sober community.

Coffee dates and/or lunch are the current standard for meeting new people. If your date chooses to drink alcohol, you should tell her that you don’t drink because you are an alcoholic in recovery. There. That’s one hurdle cleared.

Four divorces is not a first-date topic, in my opinion. Your first date should be devoted to covering more superficial basics and doing a lot of listening. If you are contemplating a deeper relationship, you should tell her, “I have a very challenging relationship history, and I think it’s only right for me to tell you about it, so you can make your own choice, with your eyes wide open.”

Dear Amy: I need your opinion on whether I am cheap, or whether my logic makes sense. When I order a mixed drink in a hometown bar, it might cost me around $4.

I will typically leave a dollar on the bar.

While on vacation I have paid as much as $12 for that same mixed drink. I know that leaving a 20% tip is the standard practice, but the bartender in both cases spent the exact amount of effort to fill a glass with ice, pour a shot of alcohol, then top it off with soda. Am I being cheap in thinking that a dollar on the bar is appropriate?

Casual Tipper

Dear Tipper: Let’s test your logic: The waitstaff at Brews and Bones in my hometown takes my order, runs back and forth to the kitchen, visits the table repeatedly and receives a generous $10 tip on a bill totaling $40.

Then I visit Le Restaurant Fancy in Chicago, where the waitstaff takes my order, runs back and forth to the kitchen, and visits the table repeatedly. This person has expended roughly the same amount of effort as the waitstaff at Brews and Bones and so, using your logic, I will also give them a generous tip of $10 on a bill totaling $125.

The waitstaff and bartenders in Chicago (or your vacation destination) likely have much higher expenses. Bartenders rely heavily on tips to make a livable wage, and often share their tips with barbacks or other support staff.

Readers: Tip generously!