Mary Chapin Carpenter and Shawn Colvin, photo by Katie Newcomb

I am asked quite a bit about what types of dates and events are good to do with a Sunday Boyfriend. My short answer is: anything and everything; anything you’d like to do is fair game and everything is negotiable with your SB (just remember your predetermined boundaries). But sometimes I get pressed for a more concrete answer. So with the start of the summer season upon us, I thought I’d throw some ideas your way. All are based on SB dates I’ve had in the past, so use these as thought starters. Bottom line: It’s supposed to be about taking chances and being comfortable with going after the things you want, so jump in and have fun whatever you choose to do with your SB.

No matter where you live, there is game somewhere. Although America’s summer pastime is better to watch in person (my humble opinion), the option to watch your favorite team from anywhere is nirvana. Unlike going to a movie, where you sit in an environment unfavorable to talking, baseball can produce many spirited conversations. Now yes, having worked for the Brew Crew I am biased to enjoying a game. So if you’re not a sports fan, I encourage you to think about it this way: spending time outdoors with a great guy while watching men in tight pants run around. Did that pique your interest? I thought so.

Cookout, Eat Out, Cooking Class (Basically….Anything With Food)
Food is a basic staple to live, and also to socialize. Want to go out with your SB but all your creativity is parked on that chair you’re sitting on? All you have to do is think food for the perfect win/win SB date. Okay, I may be getting dangerously close to crossing the “food for fun” boundary; to which I say things are always better when you get comfortable with having fun with food (I see your dirty mind and challenge you to actually do it). But seriously, ask your SB to dinner, invite him to a cookout, have a tailgate at a baseball game and double the SB fun, sign the two of you up for that Thai cooking class you’ve always wanted to take, or have a whip cream party for two; carte blanche.

But if you find yourself tapping into the great food card to get something started with your SB, you must…and I can’t stress this enough…you must be prepared. If going out to a restaurant is on the docket, have at least three restaurant choices at the ready. Rather have a cookout? Then do your due diligence and offer a traditional and signature-to-you menu. Sign up for the highest rated cooking class. And, most importantly, have at least two cans of whip cream chilled in the refrigerator. The food option is only as good as the thought you put into it. You seriously don’t want to waste time driving around to find a place to eat, losing interest in a lackluster class, or opening up your refrigerator to find a lonely jar of pickles and sad-looking wedge of Colby jack cheese.

Art Museums
This is the option to choose when you’re really in the mood to candidly chat. I find when I’m surrounded by pretty things my mind lets go and I become a bit more honest during discussions. I’m not entirely sure why, and maybe this won’t work for you, but I think it has something to do with being in an environment that exudes raw emotions. So if you’ve had a bad or rough week and need to get some things off your chest, choose a Sunday Boyfriend who is great at listening, and sink into a Monet, Miró or Matisse.

You say you’ve never gone to a fundraiser? Wow…then you’re missing out! Fundraisers can be the most ideal SB date for a myriad of reasons.

One: All the hard work is done for you.
You want to eat? Fundraisers, especially galas, provide substance. Check.
You want entertainment? I guarantee there was a committee in charge of providing all the best offerings to fit a fun theme. Check.
You want to people watch? How does a room full of coiffed folks sound? Check.
You want a reason to wear that little black dress that’s been sitting in your closet with the tags still on? Check.

Two: You get a different kind of warm and fuzzy feeling.
Even if, heaven forbid, you and your Sunday Boyfriend have an off night, knowing you are at an event that is helping someone raise awareness for a shared human experience/condition should make you feel good about yourself. And it doesn’t matter how much you are able to give financially or in-kind with your talent and/or time; the warm and fuzzy comes through with your willingness to participate. And there should be more participation in the world, don’t you think? So think of a cause that is close to your heart, and check out their website for upcoming events. If you like this idea, here is information on a Milwaukee-area fundraiser to get you and your SB started on creating those warm, fuzzy feelings. And don’t worry about how much you can give, remember it’s all about participating.

I can’t live in Milwaukee, the summer music mecca, and not mention concerts, right? Music, like food, is a magnet that brings people together. We all have moments in our lives where a song plays an integral part of establishing a memory about a certain event or person. Heck, I wrote a whole blog post about the songs that remind me of each of my Sunday Boyfriends. So why not enjoy going to an outdoor concert this summer to not only enjoy the weather, but to also create new, or solidify new soundtracks for you and your SB? Be it in the mid-day sun at your favorite church festival, under your favorite amphitheater, or with a picnic dinner under the stars, it is a very comfortable SB date choice.

Whatever you decide to do this summer, or any time of year, with your SB, remember the SB motto, “Comfortable. Always There For You.”, and confidently take the reins to do whatever it is that makes you happy.

As always, stay comfy and be good to yourself and your Sunday Boyfriends.

If you are looking for more SB information, check out our blog, our Facebook page, or Twitter.