“Should I Meet Up With My Old Friend?”

My old friend, Grant, texted me four years ago to wish me a happy 50th birthday and suggest we catch up, but I did not reply. I first met Grant in high school, and he has always kept in contact with me, even after he married. Actually, the last time I met up with him was 11 years ago and, from memory, he was almost begging me to visit him and his family. We are the same age and get along well. He is a confident person with a great sense of humor. People gravitate to him because he is very funny.

Last week Grant texted me again saying it’s been a long time and he would love to catch up. I did not text him so he rang me, but I did not answer the call. I eventually texted him to tell him it was a great idea and that I would get back to him to arrange a catch up date. The reason I am hesitant about meeting up with Grant is because he has achieved so much and, compared to him, I feel like an underachiever and a flop.

Great got married, raised four kids, is a very successful businessman, and has become wealthy. I never married (I have had relationships though) and I have no children. I have a respectable job but never reached any great heights career-wise. I do own my own apartment which I am proud of, but that’s about it.

Compared to what Grant has achieved, I feel like I’ve achieved nothing. I’m sure he’s worked hard for his success, but I feel intimidated by it. Is there any way to get out of this mindset? Should I meet up with Grant? — Feeling Like a Flop

Part of what makes intimidation so powerful is that so much of it is inspired by fantasy or imagination. Think of social media and the way it allows people to share the highlight reel of their lives. Their contacts see that highlight reel and then use their imagination to fill in the gaps that remain to create a picture of someone’s life that will be much more charmed and idyllic than the reality. And then what happens is we compare this fantasy of someone else’s life to our own reality and OF COURSE we are always going to fall short in comparison. Because fantasy vs. reality isn’t a fair comparison. I imagine this is what you’re doing with Grant.

If you haven’t seen Grant in 11 years and you’ve been in very minimal text contact every few years, I assume that what you know about all of his success is what you have gleaned from what has been shared publicly – either through social media, through gossip with mutual friends, or maybe even through news or Google searches. But what you’ve heard is only a part of Grant’s life, and it certainly isn’t the full picture, just as your respectable job and your apartment aren’t the sum of your life.

Both you and Grant are so much more than how much money you earn, where you live, and your marital status. I imagine you must have engaging qualities to keep Grant reaching out to you after all these years – and through multiple rejections from you. Those qualities are who you are and what Grant is interested in. YOU are who Grant wants to spend time with, and if you were truly a flop of a person, I don’t think he’d still be trying to connect with you after all this time.

But the bottom line is that if you don’t enjoy Grant or you don’t like who you are or how you feel in his company, you’re under no obligation to spend any time with him. You can simply continue to avoid him as you have and to ignore his texts, and eventually he’ll stop trying to contact you (and if he doesn’t, you can always block his number). But while avoiding Grant may help you avoid any negative feelings being around him might inspire, I don’t know that it will make you feel good about yourself. And maybe it’s possible that meeting up with Grant might do that? I know that when I meet up with an old friend I enjoy, who truly enjoys me, too, and cares about me, I tend to leave the interaction feeling good about myself.

If you think there’s a possibility you might actually enjoy spending time with Grant, set something up. The worst that happens is that you DO end up feeling like a failure in comparison and you vow never to meet up with him again. And won’t that actually save you time in the future? At least then you’ll know for sure that this isn’t a healthy dynamic for you and you can stop responding to him if he reaches out again.

On the flip side, maybe connecting with Grant in person will be fun and will give you a fuller picture of his life and an appreciation of his full humanity. Maybe it will even give you an appreciation of YOUR full humanity. Or maybe it will simply be a fun couple of hours with an old friend who is very funny and can reminisce with you about a simpler time in life when the trappings of adulthood had yet to burden you.

At any rate, unless you really think meeting up with Grant will nudge you into a depression you can’t crawl out of, I think you should see him. And if you think meeting up with him could potentially depress you to that level, I think you should see a therapist instead.

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If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.