Should She Spend the Weekend With a Guy Who’s Waving Sooooo Many Red Flags?

So I like a guy and we’re talking about a dirty weekend away. Sarcastic “big wow” for most, but actual “big wow” for me. I haven’t had much luck with men: shitty controlling relationships and borderline consent/rape situations. Effectively I have issues trusting men and my defense mechanism is to run away. Consequently, I haven’t been in a relationship for ten years. Also just to overshare, because that is the joy of this column: I am (unfortunately) straight, I’ve never had an orgasm, and I live in a country without a legal/ready supply of weed.

So it is an achievement for me to meet someone whose bones I want to jump. But the guy has red flags all over him. He’s never really been single and he’s a serial monogamist. Until very recently he was in a pretty miserable relationship. She was a nice sweet girl, if a little bit of a walkover, but she’d put on weight and they’d stopped having sex. When I last saw him about two years ago the chemistry was intense. He would light up for all to see when I entered the room. Somewhat confusingly, his girlfriend actually thanked me for cheering him up. But if I’d let him, he most definitely would have cheated on her with me. I didn’t entirely behave myself—I enjoyed the attention—but ultimately made it clear it wasn’t going anywhere while he was occupied.

So two years later, fresh out of his relationship, he contacts me and, well, he gives good text. So while my short term plan is to literally ride it out, what is your advice for dating someone who in my view has hung out in definitive DTMFA territory in prior relationships?

Please Say It’s Okay

It’s okay to wanna fuck this guy, PSIO, and it’s okay to go ahead and fuck this guy. Just wanted to get that out of the way right at the top.

As for those red flags that somehow consign this guy to permanent/preemptive DTMFA territory… well, let’s take them one by one, shall we?

1. He’s never been single. Okay… so he’s never been single. There are lot of good and decent and fuckable people out there that the same could be said for. Some people move from relationship to relationship pretty quickly. That might be proof someone’s foolhardy and/or a little too quick to commit, perhaps, but it’s hardly proof they’re a piece of shit.

2. He’s a serial monogamist. Okay… most people are these days, PSIO. “Monogamy used to be one person for life,” as Esther Perel says, “[but] today, monogamy is one person at a time.” The fact that he’s had a series of girlfriends and that all of his relationships have been monogamous also isn’t proof he’s a piece of shit, PSIO; it’s only proof he’s living, breathing, dating, fucking today.

3. He was in a “pretty miserable relationship” until very recently. Again, there are lots of good, decent, and fuckable people out there that the same could be said for. And was their relationship sexless because she’d gained weight and he stopped fucking her because of the weight gain and he’s an asshole? Or did she gain the weight because the relationship was miserable and sexless and she was unhappy and wanted out? You also say she thanked you for “cheering him up” by entering rooms. Maybe she wanted you to fuck him so she wouldn’t have to?

4. He was attracted to you and he might’ve fucked you two years ago, PSIO, despite the fact that he was in a miserable and sexless relationship at the time with a woman who thanked you for entering rooms. First of all, you can’t know for sure that he would’ve gone through with it. Lots of people are tempted and walk right up to the line and then pull back. But even if he would’ve fucked you, PSIO, once you made it clear you had no interest in fucking with him while he was with someone else, he stopped contacting you. He didn’t ask you again (it doesn’t sound like he ever asked you explicitly), he didn’t drunkenly slide into your DMs at 2 AM, he didn’t send you unsolicited dick pics on major holidays. He took your “no” for an answer. And it was only after he was single again—it was only after he met your stated criteria for even considering fucking him—that he reached out to see if you were still interested in fucking him. And you are!

Red flags? Pfft. Pink flags, at best, and pretty pale ones at that.

But while I definitely think you should fuck him, PSIO, I don’t think you should go away for a weekend. While it may sound tempting, PSIO, you can’t easily flee a cabin in the woods or wherever you’re talking about weekending. Maybe that’s the point; maybe you want to make it a little harder to run away. But it would be a mistake to set that kind of trap for yourself. Get together for one night someplace closer to home—someplace more easily fled—and see how that goes before you make plans to spend an whole weekend away with this guy. (Also, you haven’t seen him for two years and the spark could be gone—or he could show up with a brand new full-face tattoo or wearing whatever your country’s equivalent of MAGA hat might be.)

And finally… it’s a fine thing to be straight, you should get your hands (and pussy) on a vibrator and see if that doesn’t get you there, and if you know anyone who’s traveling to a U.S. state with a legal, recreational weed market, DO NOT ask that person pick you up a few pot chocolates. (They SHOULD NOT remove them from the packaging before bringing them home to you because they SHOULD NOT get your pot chocolates in the first place.)