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An old friend made a pass at me. If I tell my boyfriend he’ll get the wrong idea, but I don’t feel good about hiding it, either.

  • Author: Wayne and Wanda
  • Updated: February 22
  • Published February 22

Dear Wayne and Wanda,

I have a friend from my college days, “Jeff.” Many years passed after college before we reconnected on Facebook. We traded some catch-up messages, until he sent a final message saying he was going to close his account down. His reasons were vague, but as I recall he essentially said his wife didn’t like “the attention” he was getting from women. He in no way suggested I was part of this. He suggested we correspond by email and expressed gratitude we had reconciled a friendship. I felt the same way. While we did have a romantic relationship in college, it was brief, and never serious, and we had a much longer and more meaningful friendship.

We have continued to trade emails over the years — no more than one every few months. Our messages contain nothing inappropriate. We talk about our relationships, work, what we’re reading, what vacations we’re planning, how we are spending our weekends, even the weather. It means a lot to me that we stay in touch and I find I do look forward to his emails.

Recently, I woke up to a strange email from Jeff — strange because it was sent at 2 a.m. and because of what it said. “I want to talk talk to you.” I emailed him and suggested his phone had been hacked. He said it had not, he was up drinking, and the only “bad behavior” was his own thoughts.

I’m not stupid and can read between the lines here. In an alcohol-infused moment, Jeff clearly wanted to talk about more than the weather. Now I’m not sure what to do about this. I enjoy the third-party nature of our friendship — how I can bounce real-life stuff off him without fear he will say something to the people involved. But I have no desire to be a distraction in his relationship. On top of that, I have been dating my boyfriend a year, and he doesn’t even know Jeff exists. This seems like a terrible time to tell him as he will get the wrong idea, but now I feel like I am hiding something. What should I do?

Wanda says:

You are hiding something. And while we’re under no obligation to disclose to our significant others the history and nature of every in-person and online friendship we maintain, this sounds like one that is in such a gray area that you might have mentioned it — or put a stop to it altogether.

What are you getting from your friendship with Jeff that you aren’t getting from relationships in your day-to-day life? Here are some things you’re getting that you maybe haven’t considered: you’re getting an anchor connecting you to a past relationship, the musings of a married man who probably shouldn’t be sharing so much with you, and you’re maintaining a “friendship” with an ex-boyfriend that poses a very real threat to the integrity of your relationship.

With all the ways modern technology allows for human connection and interaction, one must be very careful about protecting the trust in his or her core relationship. No rule says you must share every text, email and message with your boyfriend, but common sense suggests such correspondence should never be secretive, and the moment we share a private space of emotional intimacy with someone who is not our primary partner, even if it’s just virtual or on paper, we are engaging in behavior that is fundamentally unfair.

Jeff is your past, your boyfriend is your present and possibly future. It’s time to take a break from Jeff and whatever nostalgia is anchoring you to him, lest the situation develop further into something that is beginning to look and feel a lot like an emotional affair.

Wayne says:

What should you do? Cut it out. Entirely. Immediately. Permanently.

And you aren’t trying to rekindle a romantic relationship, right? Right? You seem so lucid and thoughtful, which is why it’s surprising that you’re also seemingly confused and befuddled with this situation. Jeff is clearly a ticking time bomb rolling out a romantic long play with an eventual endgame of him making a serious pass at you. Do you really want or need that? Are you enjoying the attention? The drama? The sneakiness of the whole thing? It all feels yucky to me, as well as dishonest to someone who truly cares about and knows you — your boyfriend.

Delete Jeff’s email address and ignore his messages. Block his phone. Dismiss any future social media outreach. Move on, for good and forever.