Dear Wayne and Wanda,
I recently connected with my high school boyfriend online and we have been messaging each other. I’ll call him “Doug.” Pretty quickly our conversations moved to texting and some days we exchange texts multiple times. Talking to him makes me feel young again in the best way. I am reminded of who I once was — I remember the feeling of having my whole life ahead of me. At first our interaction was purely friendly but as time has passed, our tone is definitely more familiar and flirty, and recently Doug has started asking me questions about the past — like whether I remember our first kiss. I think that was the first time I felt like he was flirting with me. I haven’t felt butterflies like that in a long time. We’ve reminisced a lot about the days when we dated and have shared that we’ve still thought of each other over the years.
I divorced a couple of years ago and have two grown children. My life is pretty routine and this is the first thing I’ve been excited about in a long time. There are, however, a couple of issues. First of all, Doug is separated from his wife, but not divorced. He tells me they will be divorcing and are just taking their time so they can do it right for their children (he has three kids about the same age as mine). Doug has suggested we meet up in a “neutral” location as the town he lives in is small and he wouldn’t want to create gossip. It is clear to me that this meetup would be romantic and I think intimacy would be expected.
My best friend “Karla” is the only person who knows about Doug and she has been everything but supportive. She said his social media is a red flag as he hardly has any friends or photos or visible activity. He told me he’s just bad at social media and is hardly ever on there. Why would he lie? She thinks his story about divorce is shady and probably a lie. And she thinks it would be a huge mistake to go meet him — that he’s likely just a bored married guy looking for a fling. Karla is a very direct person and I feel she is being judgmental and even a little cruel, not taking into account what unexpected joy this is bringing me.
So I guess I am wondering, should I meet Doug for a romantic weekend? Or should I listen to Karla and back off? Or should I tell Karla to let me live my life? I’d appreciate help.
Wanda says:
I hate to say it, but Doug is definitely giving bored married shady guy vibes. That doesn’t mean he isn’t crushing reciprocally on you; he may find just as much throwback happiness in your text-flirting as you do, maybe even more. But it may mean he’s in no position to start a relationship rooted in trust and respect.
Even if Doug intends to divorce, there are questions here. Does his wife know that’s the intention? What’s his timeline? Have they taken any formal steps in the process? No one wants to feel like a nag or skeptic, but you also don’t want to be gullible and used. If you’re entertaining some kind of actual romance with this guy, you have a right to ask these questions and receive honest information before you make big choices.
The scrubbed social media and suggested meet-ups in neutral territories are certainly red flags, though. Your friend may be coming at it the wrong way, but she is coming from a place of protection for sure. No one wants to see a good friend used or hurt, especially when that person is coming from a place of vulnerability. You sound like a kind, open, caring person who has a lot of room in her life for love. Does Doug have room for you? It doesn’t really sound like it. My advice: Use these flirtatious conversations as inspiration to put yourself out there and try dating, and step away from Doug until his divorce is legitimately final.
Wayne says:
Who needs Wanda and Wayne when you’ve got Queen Karla kicking the cold hard facts? And if you think Karla is too direct, you probably shouldn’t have come to the W&W tag team with your drama, because as Wanda already spelled out in her response, we’re going to bring it to you raw like sushi.
Me? I wouldn’t trust Doug as far as the best process server could throw his nonexistent divorce paperwork. You may never know how much of what he’s telling you is truth, lies or gray area, but I’m confident it isn’t 100% truth. And I hope that you’re not naïve or overwhelmed by warm feelings enough to not at least appreciate that he’s on the hunt and you’re taking the bait, and he’s going to continue saying all the right things to keep reeling you in.
That said, I also wouldn’t let Karla’s views on this situationship inform your decision on whether to meet, continue conversing or cutting things off with Doug. Take it as a different, valued perspective. While she might have your best interests at heart, she can’t really understand how lonely you are and how exciting this rekindling with Doug is for you.
What this all boils down to is what level of risk are you willing to take. Can you handle a slice of romance followed by serious heartburn and heartbreak? Can you envision yourself as a side-chick with regular meetings at clandestine locations and not much more beyond texts and phone calls? Can you put up with endless unknowns, including an ever-changing timeline of if/when he is getting divorced — all coming from a guy you kinda knew a long time ago as a kid and barely know now? Or can you put yourself in a space where you are in charge and can safely separate passion and affection and getting what you want/need/crave with actually falling for this guy and making yourself vulnerable?
Close off the noise from both of them for a moment. Try to dial down all of those warm feelings. Heck, forget about Wanda and me, too. Take a deep black-and-white dive into what’s best for you and what level of drama and control you can handle, because you will be tested if you continue down this road. Then make your decision accordingly.
[Wayne & Wanda: My husband has been having a secret, yearslong emotional affair]
[I’ve started dating my high school sweetheart again, but it seems he hasn’t grown up much]
[Wayne and Wanda: My husband has been sneaking around to visit and chat with his ex]