The fact that you are having a sex-only deal with a guy who is having sex with others is pretty much a sure sign this is going nowhere. Relationships are about emotional connection, not about sex. Sex is so easy to come by but emotional attachments are not, especially on the guy's part. And just because he remembered you from 20 years ago, does not mean it was because he fondly remembered you as relationship material. He remembered the one night of sex, he took a chance, and now he has had many nights of sex with you.
So, I am not a fan of a woman initiating any sort of relationship talk but you really have no other choice. Waiting will only get you more of what you already have with him. Go ahead and talk to him. Be prepared that since you are already having sex, his likelihood of wanting to add in dating and/or a relationship isn't high. He already took the easy path with you and if he wanted to date you, he would have been down that road already. Oh, and there is as likely a chance he will use avoidance techniques to keep having sex with you while avoiding committing to you or not committing to you. Some guys know full well that to be honest will end their booty call, so they beat around the bush and say things like "I want to take it slow". Puhlease. Drop him like a bad habit if he does that, well, unless you are super happy being booty call without it going anywhere? The thrill of hot sex usually fades at some point when you realize the guy is only in to you for your body and not much else.
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The previous poster said it well. There's little chance that this relationship will be more, at least not in a lasting way. You've already defined the terms. If he wanted to date you, he would be.
Yes, you should be bold enough to ask him out. Waiting is never a sure way to get what you want. Best of luck.
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