Ten Years Later, Should I Ask My College Friend How He Really Felt About Me?

Okay, this is really, really it — the last advice column that won’t be only for subscribers. I’ve been working to increase my subscriber-only content, to be fair to those who are able to support this newsletter financially. There will still be free letters, I promise, but more good stuff for paid subscribers, too.

Here’s this week’s letter. (And as a reminder, please email me at hbschwyzer@gmail.com if you have questions you’d like answered in a future advice column!)

Dear Hugo,

Nearly my entire college tenure I was in (unrequited) love with a close friend -- and as far as I (and all of our friends were concerned) the feelings just had to be mutual. This guy would compare class schedules with me and pick up electives just so we could take classes together. He'd always offer to walk me home from parties, or late-night film screenings. He would often show up at my house with dinner or dessert for us to share, completely unannounced. He even baked me a cake for my 20th birthday, and told me it was the first time he had ever baked a cake before! Through a solid year and a half of this treatment, neither he, nor I, ever made a move.

When I started dating what would be "My College Boyfriend," my friend would still show up to my house unannounced, only to shuffle home in disappointment when I was too busy to hang out or at my new boyfriend's house. After "My College Boyfriend" dumped me, my friend was right by my side again, eager to comfort me and pick up the pieces. He later revealed to me he thought my boyfriend at that time was "kind of an asshole." And so we went on like that for the next two years, again with no advances to speak of. 

I always blame my failure to take initiative on the fact that I was so insecure back then about anyone finding me attractive -- much less the person I had a multi-year crush on! I also was afraid if it were to go badly, we wouldn't be friends anymore and I hated the thought of that. I told myself he felt the same way too, but the media had me believe that "men don't think like that," so I was stuck between thinking he either felt the same way, or did not think I was attractive in the slightest. 

We are now a decade removed from college, and our friendship has dwindled to an annual post on one another's social media for a birthday or a "like" on an Instagram post. Both of us are happily married off, and while I am very much in love with my spouse, I sometimes find myself wondering what if my friend was supposed to be "My College Boyfriend" instead of that other guy. More importantly, I just wish I knew if he really did like me, or if it all was a fantasy I had all those years ago. 

I know it doesn't change anything, and that I would never act on anything as a result, but assuming my inquiry would be purely a fact-finding mission, is it completely crazy for me to reach out to him and ask? I am so curious if it was all in my head and even if it was, I just want to know once and for all. 

Sincerely, 

Did He Love Me? Or Love Me Not? 

Dear DHLMOLMN,

If you’ll forgive me, I want to start the answer with something I wrote on Facebook last year:

A woman who was my student in 2011 messaged me recently.

"I just would like to know for my own personal contentment," she wrote, "if I had made a move in your office hours, would something have happened?"

(I don't get many of these messages, but I get some. People who know my past are curious about why I “chose” the students to sleep with that I did, and not others. )

I do remember this student, but not well. "I'm sure something would have," I say, because it's probably true and it's what she presumably wants to hear.

I was also on edge as I typed that -- sometimes people want to play out a fantasy about what might have been, a little erotic reverie designed to put to bed a lingering curiosity.  I've been around long enough to know this can sometimes be a slippery slope. Talking about what might have been can sometimes be more dangerous than talking about what was. What was meant to bring closure can instead awaken the proverbial sleeping dog. 

My safety and my relationship come first. So as I acknowledged the obvious, knowing me and remembering her, that it would have happened had she wanted it to, I do not add the intensifiers: No "Ah, too bad we missed out" or an "I bet it would have been hot."  If I’m not careful, within a few seconds we’ll move to talking about what we might have done together on my desk, and then we’re in a genuine danger zone.

I don't blame someone for asking me a straight yes-or-no question about the past. That’s fair game. But for everyone's sake, I need to be desperately clear that somethings are not only best left unexplored in deed, they're best left unplayed out in conversation.

A number of people who read that Facebook post took that as a universal warning against the temptation to dig into one’s past.  Based on your past comments, I know you read that post too, and may have drawn that same conclusion.  I’m glad your question helps me clarify.

There’s a big difference between seeking clarity about the nature of a long friendship on the one hand, and casually wondering if one’s sexual interest was briefly reciprocated.  This former student of mine was simply curious, perhaps just playing out a fantasy in her head.  Because it’s entirely grounded in something sexual, there’s nowhere for it to go in conversation except towards the erotic. Once you affirm that you both missed out on “something hot,” the urge to start discussing the exact nature of what you missed can become overwhelming. More than one sexting relationship or open affair has begun exactly this way.  I’ve been down that road too many times, and it has cost me far too much, and I know I ain’t the only one.

I share all this because your situation is fundamentally different, and I have a fundamentally different answer for you. 

Your college friend was an enormously important person in your life, during some incredibly significant years.  You were more or less best friends for a time, and the ambiguity in your relationship was evident to others as well as to you.  You acknowledge that it was your own anxiety and poor self-esteem at that time that held you back from trying to see what else might have been there.

You’re not considering writing him with an idle “Did you want to jump my bones too?”  This is as much about your growth these past ten years as it is about this man you knew.  Before, you couldn’t ask “what’s going on between us” because of a host of fears and self-doubts that you have worked so hard to overcome.  Writing to ask him about it now isn’t about kindling something that didn’t have a chance to spark, it’s at least partly about measuring your own growth. 

You aren’t doing this because you’re restless in your marriage, or absent-mindedly horny.  You’re doing this because you deserve to get the answer to a question your younger self was not prepared to ask.  This is, I think, about healing.  To use an old accounting (and movie) phrase, this is about “drawing a line” under something that has remained unresolved in your mind for a third of your life. 

A few caveats: 

You don’t mention if you’ve spoken about this with your spouse.  Every marriage has its own rules, but if you haven’t asked them, is there a possibility that they will interpret your reaching out to this old friend as a sign of dissatisfaction?  If you don’t tell them what you’re planning to do, and they find out later, will they consider it an act of betrayal?  I suspect you’ve already worked through this, so I’m raising this as much for other readers in similar situations as for you.

It’s also worth thinking through your own reactions to what you hear, too.  If you do hear an “Oh my God, yes, I felt the same way!” how do you think you might respond?  How much do you want to invest in talking through your mutual inability to name what you both felt?  Will you be able to stop the conversation if you sense that all this happy discussion of the past starts to shift towards something else?  In other words, we often tend to think we’re getting closure – when we’re in fact opening something up.  How will you shut what you’ve opened, if you need to?  Saying, “He’s happily married, and so am I, so there couldn’t possibly-ossibly be a problem” may not be quite the vaccination against trouble you imagine.  You may be sure of your reaction, but be surprised by his!

If you hear that your feelings weren’t reciprocated, or if for some reason your friend doesn’t take your query well, will you be able to be at peace with that?  If it brings up memories of past periods of low self-esteem, will you have someone safe and loving nearby with whom to process through that?  (Obviously, I hope and even expect that won’t be the case, but it would be wrong of me not to mention it as a consideration.)

If you’ve thought all this through, as I bet you have, then I think you’re ready to reach out, if you still want to do so.  I hope that whatever you hear, it gives you what you want and need and deserve.