Dear Love, I met this guy on Bumble and we just went on a second date. He calls AND texts. I'd definitely like to go out with him again, but there's one thing I'm not sure how to handle. On our second date he took me to a really nice restaurant, but I noticed he was checking out other women. He even flirted with the waitress! Also, he brought along his best friend and his best friend's girlfriend. I'm sure they were there to check me out. I played it cool, like, no big deal. But when we go out again, if he does it again, I don't know if I should say something or just not go out with him again. He even mentioned something in a text about all these women messaging him. I told him that was true for me, too. Usually I'd be done, but maybe I should give him a pass because he's newly divorced and doesn't know any better. I"m sure this guy is into me. He called me the other day to get an opinion about some outfit he wanted to buy. We're both into fashion, which is rare in a straight man and I really like that about him. Thanks!
Dear Not Sure,
Leave your uncertainty behind, girl. This guy IS into you. So much so, he's trying to get you to drop your facade of nice. I'm not suggesting he's being intentionally manipulative. Some people are naturally competitive, and they operate by seeing how their opponents react. And yes, I'm using that language specifically. For now, let's stick with the shitty behavior.
It's not all that surprising. He's not going to announce, "Gosh, I'm so lonely since my marriage ended, I just want to find someone to fill that void." But this reads like that exactly where he's at, so he's going to pretend everyone wants him. This is a show. He is performing because he's trying to be impressive. If you are interested in him, the best response is to not give him an audience. Even stronger would be to play along, with glee. Flirt with the friend he brought (we'll be coming back to that, which, btw, is SUPER WEIRD). Flirt with the person who fills your water glass. But most importantly, don't take that behavior on board as a sign of your unworthiness. Because that is the blood in the water that this person is looking for.
Unfortunately, you can't fake this. If there's one-upmanship, or anger, even in a text, it comes across. Then he knows he has you. Frankly, this makes the competition less interesting for the player. So if the behavior is leaving you deflated, you should probably do some more investing in yourself. I don't mean spending money on clothes or facials, but taking yourself on dates. Treating yourself the way you would want to be treated. Yes it sounds corny, but when YOU become your favorite person to go out with, you will be able to shut this kind of thing down so much faster.
But my sense is that this isn't truly your problem. You like yourself enough to know that you don't like this behavior, BUT (it's a big but, because you're obviously smitten), a double with his best friend on your second date? That was standard 40 years ago maybe, but not now. There is such a huge hurdle to get over in terms of getting to know someone, that splintering attention like that is odd. It would be one thing if you were going to a concert or some kind of event, but over dinner? That's intense. Though, truth be told, this started to bug me way more after reading your last lines. He called to get your opinion on his outfit? Yikes!
I'm sure after two dates you don't know what his relationship with his ex was like, but if you want to date him (or any successful person, which I'm guessing is part of the appeal), you want to get a sense of how he views intimate relationships. Does he laugh when someone refers to their partner as, The Warden? Or say things like, "If you're wrong and you shut up, you're smart. If you're right and you shut up, you're married"? If so, you may be dealing with someone who thinks the phrase intimate partner is on a par with enemy combatant.
Not Sure, this guy is so into you, he's trying to Wife you. After two dates, he should not be calling to get your opinion on an outfit. That's too much. Sadly, it probably is because he's just uncoupled, and you're right, he doesn't know how to date. I'm guessing you helped him out with that, but the best response would've been to say you couldn't talk, and then drop the thread. Allowing yourself to be Wifed too soon kills the thrill for everyone. You begin to feel like an old shoe, and they treat you like one. I had a guy with fresh divorce papers do this to me once, and after two dates, when he called repeatedly, knowingly interrupting the time I was spending with a friend. Finally I picked up, only to learn he was having printer problems. I told him flat out, "No. This is not an emergency, You need my address to send flowers? That could be an emergency for where we're at. But your printer? Don't call again."
Obviously, I wasn't so into him.
The only thing you need to get sure about is if he's worth sticking with. The whole thing about the other women, at this point, is trivial. It's showing off and kinda gross, but not yet a real problem, and you're likely to encounter this kind of thing again. People who really are scoping out their next date don't typically announce it. But if he's the kind of guy who goes out of his way to make you uncomfortable, by, say, texting you how desired he is, is that the kind of guy you want?