If you enjoy the column below, please subscribe to my newsletter! You’ll get each new issue in your inbox for free. I love having new email friends.
And if you’ve got a problem you’d like me to solve, send it in via my anonymous form. Let’s open some letters!
My very close friend passed away three years ago. After she passed, her husband and I spent a lot of time together as she has two daughters that my daughter and I are very close to. Recently we began a physical relationship that has quickly morphed into something more. We have very good communication and talk about what this could mean to our friend group. Nothing was planned. We never crossed any line while she was here. We are enjoying each other and the ease of our situation.
We’re not in a relationship, but not opposed to that being the next step. I don’t feel guilty, but I’m honestly not sure if I should feel guilty about everything. What do you think?
I think “Should I feel guilty about this?” is standing in the way of two better questions to ask yourself right now:
1. Who is at risk of being hurt by this?
2. What do you owe those people?
I can’t tell you whether this relationship is right or wrong, but your answers to those questions might give you a clue.
Take, for example, your friend’s two daughters. Would they find comfort and stability in this new relationship, or would they be disturbed by it? The husband’s first priority needs to be his kids, especially in the wake of such a significant loss in their lives. If they’d be happy to wind up in a Brady Bunch situation with you and your daughter, great. But if this is going to cause them further distress, or fracture their friendship with your kid, I think you and this guy have an obligation to pump the brakes.
And then there’s your friend group. I think you’re right to consider their reaction to all this — not only because you care about their feelings, but also because their view on this as objective observers would be telling. It’s impossible for me, a stranger with two paragraphs of context, to know whether you’re in the middle of a beautiful love story or a troubling betrayal. But your inner circle would probably have a hunch.
I think guilt is a thing you’d only arrive at by hurting the people you love. There’s no need to preemptively resign yourself to that fate. See if it’s possible to approach this with tact and care. If it’s not, ask yourself why.
I am going to a small wedding for one of my childhood friends (Janis) next month. I asked her who of our mutual friends will be there and it turns out the only people I will know are her parents, siblings, and one girl (Regina) from high school who has always been rude to me, and is not someone I enjoy being around.
I haven’t seen or spoken to Regina in six years and it’s likely we’ll be in unavoidably close proximity for a couple of days. How would you suggest navigating hanging out/avoiding hanging out as much as possible with Regina and enjoying Janis’s wedding?
—Feeling Like Cady Heron
A lot can change in six years! You might enjoy the wedding more if you’re open to the possibility that Regina has grown in that time. Especially since you won’t know many other people there, the benefit of a familiar face could outweigh whatever bad feelings still linger from high school.
But, okay, let’s assume you go in with an open mind, and she still sucks. And just to make my job harder, let’s assume there’s no escaping her. You’re stuck in the bridal suite getting your makeup done together, you’re seated at the same table for dinner, she follows you onto the dance floor for the Cha Cha Slide, etc.
I think if you can’t get away from someone, you might as well get curious about them. Set aside the question of whether you like this girl — it barely matters, you don’t have to see her again after the wedding — and instead try to figure out what makes her tick. You might be surprised by the new things you see in her now that you’re both adults. Maybe you’ll realize, for example, that her rudeness comes from a place of social anxiety, or insecurity, or unhappiness in her own life. Maybe you’ll find new ways of engaging with her that make her, like, 20% less awful. Or maybe she’ll be a total monster the whole time and you’ll get a good story out of it.
Approach the whole thing with more amusement than anger. If you’re a writer, use your time with her as inspiration for your next villain. If you’re a scientist, make her your secret research subject for the weekend. If you’re a teacher, see if you can unlock some thrilling new ways to manage bad behavior. There is so much you can do with a person besides enjoy them. Good luck.
I am grieving the end of summer by drawing summery things. Here’s a ladybug and a watermelon.
I recently met this guy and we completely hit it off. We have very similar interests, a similar sense of humor, and overall just have really great chemistry. Not to mention, this guy is legitimately just one of the sweetest people I have ever met. Unfortunately, when I met him and asked him out, he had just gotten out of a relationship that was a little over a year long.
After our first few dates, he confessed to me that while he really likes me, he thinks he tried to rush getting over his last relationship and needs some time to be single. He told me he’d still love to hang out as friends. I told him I was OK being friends for now, but that I intend to ask him out again at some point in the future. He said he was OK with this, but obviously couldn’t guarantee a yes because grieving a relationship doesn’t exactly have a timeline.
Right now, I plan on waiting a few weeks so he can process his relationship before asking him out again. Am I being naive here? Do I actually have a chance with this guy?
I’ve got a few different voices in my head shouting over each other right now.
The optimist in me wants to believe you have a chance. It’s rare to connect with someone as deeply as you’ve connected with this guy. That’s worth holding onto, so long as you’re sure the feelings are mutual.
The cynic in me wonders if the feelings are mutual. There’s nothing wrong with the fact that he needs time to heal from his last relationship, but I’m curious why he’s already bracing you for the possibility that he’ll reject you again in the future. I tend to think that if he were feeling the exact same feelings as you, you would not be confused about it.
The pragmatist in me thinks the ball should be in his court, not yours. Why should you have to guess when he’ll be ready for another date when he could just tell you? The pragmatist would also like me to note that the wait might be longer than a few weeks. If he’s saying he needs time to be single, I’d assume that time will be measured in months, not weeks.
All three of these voices in my head are loud, but the pragmatist is probably the most correct. The next time you talk to this guy, I think you should amend your previous plan: He should be the one to ask you out down the road, if and when he’s ready.
In the meantime, you can stay hopeful about this guy. But stay open to others, too.
This is the part of the advice column where the lights turn on and the credits roll. But before you go, I hope you’ll subscribe to my free newsletter! You’ll get each new issue of Stephen Please directly in your inbox, and it’s completely free.
And don’t forget to send me your problems via my anonymous form. See you next week!