When meeting someone new, it’s tempting to want to start on a clean slate, but no one ever does. We’re all a collage of different dating and life experiences that make us who we are. That’s exactly why hearing about his dating history and learning as much as you can about it is really important.
He’s not be over his ex.
If he doesn’t talk about his exes then you might wonder if he’s hiding something, and he very well might be. The worst-case scenario is that he’s not over his ex. That’s definitely not a clean slate.
He hasn’t been single that long.
“When was your last relationship?” is one of the most important questions to ask a guy you’re dating. Imagine if he’s only been single for two weeks and he’s rushing into something new with you. No way – that screams rebound. It’s important for him to have taken the time to go through the breakup and firmly close the door to his past. That doesn’t happen in two weeks. Sometimes it takes two years!
He has destructive patterns.
You can read between the lines of what he says about his previous relationships to find out if he’s got some unhealthy dating patterns. These are important to know because they’ll directly affect you. For example, he might be the type of guy who dates and then dashes because he can’t handle commitment. You don’t need that drama in your life.
He’s best friends with his exes.
If he’s best buds with his exes — as in they still hug and kiss and see each other every weekend — that can definitely ruin your relationship mojo. That’s not to say they can’t have platonic friendships, but it’s not a good sign if he’s hiding this stuff from you. Also, how can every single relationship end amicably? It just seems a little hard to believe…
He has little to no experience.
A guy who hasn’t dated much shouldn’t be a red flag unless he’s quite immature in the dating game or he just doesn’t know how to be in a long-term relationship. Hmm, those are definitely warning signs, which is why it’s good to understand where he’s coming from and where he’s been (or has yet to be).
He’s a player.
Not every guy who cheats on his girlfriend is going to repeat the behavior in future relationships, but come on! You want to know if he has a dating history filled with infidelity, especially if he was the one committing those sins, right? Of course you do, and you have every right to. It helps to know what you’re possibly dealing with so you can be a bit more prepared and maybe guard your heart a bit more until he proves himself.
He hasn’t learned from his mistakes.
One of the most important things about our relationship history is that it can show us how far we’ve come. Has this guy learned from previous relationships and the mistakes he made in them or is he quick to call all his exes crazy and unreasonable? Ugh, the latter points to a guy who can’t take any responsibility for his life.
He’s still in a relationship.
You might think that he’s moved on from his past because he’s on a date with you, but who’s to say he’s even over his past relationship? He might still be in it! He’s probably not going to admit that right off the bat if he hasn’t before your first date (jerk), but asking him lots of questions will help you get some hints so you can run for the door.
He could be a love-bomber.
How long were his previous relationships? If he hasn’t been in a relationship that’s lasted longer than two weeks, you have a problem on your hands. Maybe he just loves the chase, or he’s a love-bomber of note. Or, maybe he’s just a dating opportunist who isn’t really setting his sights on something real.
He’s a sexist.
It’s a pity you can’t interview his exes to find out what he was really like as a boyfriend, but that doesn’t mean you can’t learn about his boyfriend behavior from what he says about previous relationships. You can suss out his thoughts towards his exes and women in general by having regular Ex Talks. Is he a sexist guy? (For example, “All women are gold diggers. My exes were.”) Does he think that women and men need to conform to gender roles? (For example, “My ex, Sandra, was always too ambitious.”) You can learn a lot about his views on equality when unpacking his dating history.
He wants the fairytale.
Maybe he’s mysterious (read: lying) about his relationship history because he doesn’t want things to be less than perfect. He’s all about having a fairytale romance, but it’s unrealistic. If he’s always painting himself out to be the perfect boyfriend who loved all his exes and treated them like queens, it’s possibly a red flag. He might be trying to convince you that he’s the perfect catch when really he’s toxic.
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