Dear Wanda and Wayne,
There’s this guy in my life, I’ll call him Tyler. Tyler and I have known each other for years and are part of the same extended friend group. Most of us are in our late 20s and we’re pretty tight. Usually, some combination of us spend holidays together, go camping together in the summer, and go out most weekends.
For years, Tyler and I have had a special connection, and things have gotten romantic between us many times. Twice, we tried dating, which lasted almost a year the first time; and recently we gave it another go, but it lasted just a few months, and we ended it this summer. There is a lot of love and chemistry there, but ultimately with both breakups, Tyler said we were better as friends and our friendship was too important to jeopardize it. While I was hurt, I understood his logic and was also thankful for our friendship and that we’d remain in each other’s lives.
Here’s where I have a problem: Both times we broke up, Tyler almost immediately started hooking up with a girl in our friend group — one girl the first time, and a different girl the second time. He tells me he can’t be with me because he doesn’t want to screw up the friendship so then he goes and gets with … one of our friends? Not only do I feel like this devalues the reason he said he ended things with me, but really, Tyler? Anchorage is full of options and you had to get with our friends? It was hurtful and disrespectful.
So I called him out on it, and he said I was being unfair, and that we never made any rules about anyone being off limits. He’s not wrong. But I still think he’s out of line in starting up stuff with women I’m friends with. Who’s right here?
Wanda says:
There are rules, and then there’s common sense, and if Tyler has an ounce of the latter, he knows good and well that if he started hanging around one of your mutual friends, it’s going to hurt your feelings and pride. After all, he’s the one who ended your relationship — both times, you pointed out — so one could deduce you’d be bummed by whoever he took up with after the fact. That it’s in your core group and right in front of your face has got to sting.
That said, there’s obviously a pattern here: Tyler is a lazy dater! Or a lazy hooker-upper, whatever the case may be. Either way, this guy keeps it close to home and in the comfort zone when picking partners. Your friend group can’t be that big, and presumably, not all the members are romantic options for old Tyler, and yet he’s managed to burn his way through three of you? Swift work, mate.
Eventually, Tyler will run out of options, and you gals will stop giving him second chances (”tsk tsk”). You know what they say: Fool me once, shame on you; fool me twice, shame on me. Your thoughts about how Tyler has treated you are still taking up a lot of your emotional real estate. You’ll be a lot freer and happier when you stop letting his actions and choices frame your feelings.
Wayne says:
Rules? What rules? There are no hard and fast rules in romance and dating, and no one in this situation is right or wrong. Not sure if you’ve noticed because you’ve both been swimming around your little incestuous friend pool, but dating in the real world is crazy. People lie. They ghost and they gaslight. They hide their baggage and surprisingly pile it onto you. They even share their dating experiences with you on social media, putting you on blast! It’s the Wild West!
So don’t blame Tyler for doing what (and who) Tyler does. Tyler’s just being Tyler and going with what’s available to him, kind of like you did with Tyler (twice). And if you’re mad with him, where’s a little fury for your “friends” who hook up with him practically minutes after he dumps you (twice)?
Now, there may not be universal and hard-set rules for dating, but you have complete control over setting boundaries and creating rules of engagement for how and who you date, and expectations for the people you date treat you. Stop letting the Tylers and the insensitive friends of your world guide how you date and how you respond and feel about it. Sure, the whole thing is awkward and even yucky. But you could take this all as a positive if you shift these experiences into a clearer road forward on your dating life, and maybe even the emotional investment and trust you put into the friends you spend your time with.
[He wanted to keep our fling a secret. Now he’s dating my friend and I look like the bad guy.]
[Wayne and Wanda: I’m dating a great guy, but my history is making me insecure]