Do you feel guilt after a "hook up" or feel you want to see her again, guys?

I had a "hook up" first time at 35. Not looking for love, made it clear wasn't before amazing night of sex with a guy. Since he keeps calling, wants to take me out on a proper date- now I feel guilty. He's a great guy but just not what I want right now and have since met another guy I am attracted to. I've told the new guy I'm not looking for anything serious, just flirt and fun, we haven't yet had sex but have booked a hotel for Friday night. But he has for the past 2 weeks since meeting been texting me everyday, some flirty, some with sexual undertones and some just how was your day. I'm not used to the texting thing, my ex texted me like twice in 17 years- can you get milk on way home? lol Is this normal- he's younger, 22 so maybe its just that he's from the tech generation and this is normal or is he already getting a little attached? I don't want to "hook up" with him and then deal with another bout of guilt because he wants a more involved relationship after like the first guy. So- is it ever guilt free, he has already said he is worried "hooking up" will hurt me, I have assured him it won't- but I am concerned that he might get hurt.
Updates:
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He has already said he is the "feel guilty" type of guy after a "hook up", I've reasured him theirs no guilt needed, but worried he will feel it anyway & not sure how he will act afterward because of this.
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Most Helpful Guys

  • First, I don't believe in guilt; I don't see the point of internalizing ill-will.

    As for you, just tell him what you told us: "[You're] a great guy but just not what I want right now." If necessary, add, "[I] have since met another guy I am attracted to."

    This is normal dating life. Any well-adjusted teenager can wish you well and shrug this off. A grown man who can't is undateable.

    Also: "he has already said he is worried 'hooking up' will hurt me"

    You didn't take him at his word, did you? From what I read, he's the worried one, not you. You have to learn to spot this, when people try to dump their issues on you. It speaks of an immaturity that will require some careful handing--or a less-careful dumping.

    • I was concerned that yes he has said he has "hooked up" before and that he felt guilyu about it and didn't want to hurt me if we ended it at that, however, he has also given the impression he is inexperienced with women and that he has been single for 2 years because he had a messy break up with his ex of 2 years- so I was worried he was actually being a little defence rather than worried about me, I'm 35 and can handle the soituation for what ever it is. Thanks for you comments, was reflective.

  • OK this may sound a little harsh, but trust me - it's OK. What you have to do is to just be honest with him and tell him how you feel about what he's doing. He's going to understand. If he's like most guys, he won't even be hurt about it. So don't worry too much about hurting his feelings or something.

    And lol, usually it's the guys who feel guilty after hooking up. Though I know a lot who have no conscience at all, and don't feel a thing about having sex with someone and then not ever seeing them again. As a guy, he should know this too. So I believe if you tell him you don't want to get attached to him, he's gonna get off your back. =p You can even tell him you're interested in someone else, it's perfectly fine.

    • I guess that's my point somewhat, I feel guilty about saying no to dating the first guy, I don't know if he is pursuing me out of guilt or interest. Either way, aside from another night of great sex, I know I don't want anything else with him- but will have to avoid even a night of grat sex as he does want to date also. Just worried the same will happen with the new guy, and being younger he's not got much experience with women- by his own account. Don't want to f*** him & crush him!

    • Aww like I said, don't worry. ^^ We tend to get over these things fast. The only time we get hurt is if we actually get attached emotionally, and he hasn't known you for that long to have a real emotional connection with you, so he's not gonna take it personally if you say no. Especially because you told him before that you aren't looking for anything.

    • Be careful. Men talk a big show, but deep down it just takes us longer to process events. He will probably get hurt and lacks the foresight to understand that due to inexperience.

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What Girls & Guys Said

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  • If you have made it clear to him that you don't want and don't expect a relationship, then just go-ahead with your plans. He has been warned and if he then gets hurt he will have to mark it up as growing pains. That's the risk a guy of 22 has to take when getting involved with a girl of 35

    • I guess because I am older & know he is at a very confusing time in his life at 22 I feel like I have the responcibility to ensure he is not emotionally damaged if he wants more and I don't. I don't want to "school" him in overcoming rejection.

    • "I've told the new guy I'm not looking for anything serious, just flirt and fun" Does he understand English? Or does he think your "No" means "Yes"

  • He will feel guilt. It's not over just you. It's also over everything he knows he should've done for himself, but didn't. As long as you don't get pregnant or anything, you need to smoothly transition him into finding someone else. Be supportive, but don't let him think he can get closer to you. You at least owe him that.

  • I don’t think you should do this without saying before hand what your intentions are. You need to also see if he is a virgin.

    It’s not a good idea if he is a virgin in my most real 💯 opinion.

    Not because it indicates anything but because he feel be more haunted by the experience that way. He won’t even realize it until it’s way too late, but he’ll realize it eventually.

    Ultimately it’s your call. However I no longer think it’s possible to have sex without pain. When a person leaves, sooner or later someone is going to feel it.

    It’s the cost of affection. And regardless of all other things, I now think female choosiness is a blessing in disguise for this reason.

  • You can give him more than he want until he hate