Wayne and Wanda: How honest is too honest in a budding romance?

Wayne and Wanda,

I’ve been seeing someone new for a couple of months now. It got very serious very quickly. I haven’t been treated this well in a long time, if ever. He’s attentive, sexy, smart, and fun. I’m learning he’s also very honest. That’s a good thing, right? I thought so too. But his honesty led him to reveal information to me that now I can’t brush off and I am afraid it may be affecting how I feel about him.

First I asked if he had ever cheated on anyone, and he said yes. He didn’t even try to conceal it. He just said in a very straightforward way that yes, he had cheated. OK, maybe I should have stopped there but my curiosity got the better of me and I asked for details. He said a few times when he was younger, he hooked up with other women when he was already seeing someone. He said he would never do it again, that these decisions left him feeling like a horrible person and he learned his lesson.

Now my wheels were turning. I didn’t know much about his relationship history, though I felt like we’re young enough (mid-20s) that the fact that he’d been unfaithful several times was slightly alarming. So I asked how many people he’s slept with and the number he told me was shocking. Shocking. I am not a prude, I am not experienced, but I found myself instantly doing math wondering how a 25-year-old guy could have possibly been with so many women.

Now I’m feeling freaked out. Have I fallen for a total player? Is he going to cheat on me? Will he get bored in a few months because obviously variety is the spice of his life and he doesn’t know how to be with one woman? Then I feel terrible for leveraging these judgments. He’s been nothing but wonderful to me and he was completely honest when I asked him hard questions. Still, my instincts are telling me to save myself and bolt, even as my heart is saying that would be a terrible waste of an opportunity with a decent guy.

Advice, please?

Wanda says:


Ask and ye shall receive, and boy did you ever. On one hand, congrats, you have found yourself an honest guy, or at least honest now that his cheating days and ways are allegedly behind him and he’s smitten with and committed to you. On the other hand, had you never asked, you’d still be happily floating along in your love bubble, which has now decidedly popped and left you contemplating the mess.

The “how many people have you been with” question is a grenade that should be tossed sparingly, only when it really matters, and only when you’re prepared for a big explosion. You described yourself as a non-prudish and nonjudgmental person. You could have avoided a world of self-doubt and paranoia had you just continued to enjoy your new romance with a doting dude.

Too late now. You know too much about his past to simply receive him as his present self, and the revelation of information has you tempted to bolt. Meanwhile, the poor guy was just trying to be honest and authentic.

The only way to save this relationship is to be completely honest with him about where your head’s at: You regret asking about his past, it’s got you in something of a tailspin, and you need reassurance that his oats are sowed and he’s serious about commitment. It’s a shame you have to have this conversation, as his present-day actions seem to show he’s ready for the real thing. But until you shake your insecurities and get further validation, you’ll dwell on his past.

Wayne says:

You want answers? You want the truth? You can’t handle the truth!

There’s a deep level of trust that comes with this type of honesty, and he trusted you enough to unload some of his deepest, darkest and even most regrettable truths. He also trusted you enough to expect that you would appreciate that those moments made him the man, lover and partner he is today, and that you would understand he is fully committed to you today and going forward.

He will not expect that you’d drop a Reverse card on the trust and truths of his past to question his current character and future intentions. He isn’t a serial cheater. He isn’t a sex addict. He isn’t a romance felon with an ankle bracelet desperately seeking a second chance at love. He’s a seemingly solid human being with a past. Hey, you have one, too, by the way — though it sounds like yours has no missteps, mistakes, one-night stands or booty calls. That seems almost too good to be true! And if it is indeed true, well, it sounds boring. Perhaps you haven’t accumulated enough real-life experience for grownup relationships, which would explain why you’re so aghast at his past.

His truths have rattled your delicate sensibilities, unrealistic expectations and romantic dreamscape. So yeah, go ahead and blow up the foundation of this relationship and undermine his trust by telling him that he was just too darn honest about his past, that he’s a naughty boy and that this past does matter today.

One day soon, when you’re single again and moving into your late 20s, going on dead-end dates and sadly scrolling on dating apps through lineups of men who haven’t moved out of their Player Eras, you’ll realize that body counts and life lessons of a good human being aren’t deal breakers but character builders, and more common than you can fathom.

[Wayne and Wanda: I asked my new boyfriend about previous relationships. Now I don’t know if I can trust him.]

[Wayne and Wanda: The time my girlfriend spends with her drama-filled softball team leaves me uneasy]

[Asking Eric: I’m in my late 30s and want to get serious. How do I deal with my noncommittal partner?]

[After 6 months of dating, shouldn’t he have told me he was still sleeping with his ex?]

Wayne and Wanda

Wanda is a wise person who has loved, lost and been to therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at