My high school sweetheart told me his marriage is ending. Should I meet with him?

Dear Wayne and Wanda,

My very first serious relationship was with “Bill.” We were high school sweethearts and dated into the college years, but were then long-distance and grew apart. Bill started dating a mutual friend, and they got married. It hurt that he got involved and then married so quickly after our breakup.

I’m now in my late 30s, and the other day received a message from Bill wanting to know how I’ve been. I was surprised; while we’re friends on social media, we’ve never directly interacted. After some back and forth, he sent a much longer message. He told me he and his wife are getting divorced. He said he’s truly never stopped thinking of me over the years and knew he wasn’t over me when he got married. He asked to meet for drinks.

I’m totally single right now, and I’ve often thought of Bill as the love of my life and regretted that we didn’t try harder to make it work. I was going accept his invitation when, of all people, his wife messaged me. She said she suspected Bill might reach out — though I’m not sure she knew he did — and warned me that they are still working on their marriage and said “don’t believe anything he says.”

I of course asked Bill about that and he said the marriage is absolutely over, and his wife is in denial. So I agreed to meet him and we have a date set in a couple weeks after I return from some business travel. My close girlfriends all seem to think I’m making a huge mistake but I feel like I need to see Bill to know where things stand after all these years. What do you think?

Wanda says:

I understand why you said yes to a meet-up. It’s normal to want to put a bow on loose romantic strings of the past and it must be validating after all these years to have Bill digitally slinking back into your DMs, being all conciliatory and contrite. After all this time you spent resenting the fact that he got over you so quickly, you can find a thrilling sort of validation knowing he wasn’t over you after all.


Or so he says. Here’s what I see: a man who doesn’t know how to be alone and in fact seems to have never really been on his own, gliding straight from his first adolescent relationship with you into his marriage that carried him through his adult years. Now that train is coasting to a stop — it hasn’t even arrived at the final divorce destination! — and he’s already looking to jump tracks to you.

I’d question whether the sentiments he’s expressed are sincere, or simply convenient and convincing sweet nothings designed to get you to make space for him. That sounds manipulative, but he may not even realize how calculating he’s being. Simply put, Bill is in survival mode. He’s a man who’s never been alone or taken care of himself. This doesn’t mean he’s a bad guy. It does mean that he’s possibly got some deep-rooted insecurities and issues to sort through. Meet up if you must, try and get some answers to questions of the past, but before you take it any further, know that getting involved with a man like Bill — someone who has never had to stand on their own — is a huge risk.

Wayne says:

Bill appearing in your DMs and getting all up in his feelings after all of these years should be a bright enough flashing neon sign saying that this is all heading toward an unhappy ending for you. The even larger red flag of his technically-still-wife pouring out her feelings to you about him pouring out his feelings to you is an undeniable indicator that there’s nothing but drama ahead should you continue down this road. Ignore these red flags and stop signs at your heart’s peril.

But this is your life and he was once the love of your life, right? Maybe, maybe not. Many folks look back longingly and lovingly at past relationships and partners — the ones-that-got-away, the where-did-it-go-wrongs, the wish-we-tried-harder, the if-only-we-had-a-second-chance. In doing so, they conveniently overlook the mismatching, annoying, painful or downright devastating factors that led to a miserable relationship and eventual breakup. These selective memories rise up more frequently when we’re in a lonely space. You may be in a funk, but Bill isn’t considering your feelings by getting back in the picture.

I think you’re remembering and feeling what you chose to right now, instead of admitting to yourself the way things truly are: that Bill’s emotional state, intentions with you, and situation with his partner — and his partner’s obsession with him and you — are a hot mess, and that these two are going to take you down in flames with them. Your true friends — and even your new friends Wanda and I — see things clearly. Listen to your friends and thank your besties for pulling you out before things got really crazy.

[My partner of 16 years, who is the father of my 4 kids, has been deceitful. What should I do?]

[My husband’s brother moved in when he separated from his wife. It’s now been 6 months.]

Wayne and Wanda

Wanda is a wise person who has loved, lost and been to therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at