Would You Loan an Ex Money? (Oh, and Toss His Salad)

I was dating a guy for three years. We had great sex and fun times but he had a few kids and I have none. Every time we would break up he’d chase me down crying like a baby for me to come back to him. He even kissed the ground for me to stay with him but the last time we ended it was through text. I don’t know, for us to end it over text is just crazy to me.

It’s been six months and I still think about him. I didn't get closure and I think that why I think about him. But, ever since we did end it things are going good in my life. I even came into some money and I thought about helping him out. Am I crazy for thinking that?

When we did have sex he wanted me to give him head while I stuck my finger in his ass. He even let me stick my toy in his ass. But, he didn't like it though he told me to TAKE IT OUT because it was too much. Do you think he was gay? He told me to never tell anybody about that part of our sex life but I did tell my BFF; she thinks he’s gay but in the closet. Have I been fucking a gay guy all this time and didn't know it? I heard that men love getting head while you stick a finger in the ass. Is that true for all men or sign of a gay man? Help!

Thanks for an interesting letter. In regards to the breaking up and moving on, what I noticed is the first thing you mentioned when describing the relationship was "we had great sex and fun times." There was no mention of how y'all treated each other, what y'all spoke about, shared goals or anything indicative of a greater connection other than "great sex and fun times." Not saying there wasn't any substance in your relationship, but it's interesting that those were the first and only words you used to describe a relationship that lasted three years off and on. Just something to take note of and to reflect on.

Also, I'm not sure as to why y'all broke up so many times over the years (you only mentioned he had kids but it wasn’t clear if that was the cause of your issues) but depending on what the issue was and how serious it was for y'all it would determine whether you guys are better off apart in my eyes. Given that there was more than one split, though, I'll assume it was a perpetual issue(s) that just didn't work in the long run.

As for the text breakup, it's kinda lame but as someone who also had an on again/off again relationship that lasted years, sometimes it's a simple thing that finally becomes your final straw. While the exchange on text may or may not have been that big of an issue in the grand scheme of things but sometimes you just come to the realization that you just can't do it anymore. In my case, the argument that finally ended it was her walking in the house with wet shoes. It sounds silly in retrospect but the breakup was building over five years and that was the spark to finally walk away for good.

Closure depends on the person. If you feel there's some unresolved matters to be addressed then handle that but stick to your guns and just say what you have to say and cut ties. Otherwise you'll just find yourself back in the same cycle again and if that isn't what you need in your life then recognize that and make changes to weed out the dead weight. You yourself say that your life is better since the final breakup; so why back track? Sounds like you're just asking for punishment in the name of "closure."

As for the gay stuff, does it really matter? From what it sounds like you guys are finally over and whether he was or wasn't you enjoyed the sex while you were intimate. Couples experiment and they say prostate stimulation is supposed to be pleasurable for guys. However, most are too wrapped up in machismo to explore it. Just because he was willing to try that with you may raise an eyebrow but he could have just been comfortable enough with himself and you to give it a try.

You also said he didn't even like it so if he couldn't handle a toy I doubt he'd want the real thing. But who knows. I can't speak for every man but I'll pass on a finger in my ass but if we’re going to be completely honest my ex and I did exchange salad tosses back in college. Did that make me gay? Nope, we were just experimenting in pleasuring each other and came across that maneuver before either of us knew there was a nickname for it (we called it cookies & cream). You live and you learn.

Oh, and if you want to loan ol' boy some money it's really your call but I wouldn’t advise it. Does he really need it? Can you afford it? Do you see this being yet another thing to tie y'all together again? Just some things to think about as you don't owe an ex anything unless it's genuinely from the goodness of your heart.

Good luck

Have you ever had an on-again/off-again relationship? How did you finally get the cycle to stop? Do you think if the first think a person mentions about a relationship is superficial or sexual that that’s all the relationship was about? Would you need closure if the breakup happened over text? Have you ever ended a relationship over something really simple? Was it just the final straw in a long line of issues/ Would you loan an ex money? Do you think the anal play they had makes this guy gay? Or should couples be open to experiment in the bedroom? Has tossing salad ever been on your sexual menu? What advice would you give this reader?

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