Relationship and Dating Advice from The Guy’s Perspective: Dating a younger guy

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Dating a Younger Guy

(Read the script while you watch) Is that even possible??

Younger guys have enthusiasm, where older guys have experience, and as we guys say, enthusiasm often trumps experience. Because who doesn’t want a partner that’s up for anything, and willing to just give it a shot, go with the flow; someone who throws him or herself into every activity with zest and full attention. That’s what you get when you choose enthusiasm over experience. Guys certainly apply this theory, because a person can be hot as all get out on the outside, and frigid as a frozen signpost on the inside. And what person in their right mind wants to put their tongue on a frozen signpost? But we digress.

Yes, enthusiasm is malleable. It can be shaped, molded, and taught. It can be sent on a bevy of errands such as: buying groceries at the store, picking up dinner, taking the dog for a walk, and fetching motrin at 3 in the morning. And in addition, enthusiasm doesn’t complain much because it’s just happy to be there. It’s happy to take part in whatever new experience you have to offer.

So a younger guy is good, but not too young of course. Please make sure your young guy is old enough not to refer to you as his Mrs. Robinson.

If you’re a single mom with kids, and currently dating a younger guy in his twenties—or at least contemplaing it— beware. He’s probably not there for the long haul, even if he’s willing to get down on all fours with your kids, and play in the mud. Because bedding a hot older woman is on the top five of every guy’s fantasy list, especially if he can play with YOU on all fours. And the minute he’s able to cross you off his fantasy list, he’ll move on to threesomes—hopefully with two women—and then the alluring and powerful dominatrix. Unless of course you’re able to cover the gammut. Then he’s there as long as you can keep it up. Kidding. Kind of. No seriously kidding. Not really.

Overall, dating a younger guy, which means someone at least five years younger than you, is a good thing to try. And once you do, you can cross this off YOUR list, and head on to some of the greater challenges and goals you might have, like bedding a professional athlete, a porn star, or the short bald older guy with a huge, um, wallet.

Until next time, This is the Younger Guy’s Perspective.









19 Comments on Relationship and Dating Advice from The Guy’s Perspective: Dating a younger guy

  1. I agree this could work, Sai, but wouldn’t recommend it when a woman has young children.

  2. I don’t think I would like being called a cougar, so if anything ever happened to Rod, I would go for the older bald guy with the big wallet.

  3. My husband is 3 1/2 years younger than me and I have to agree with you 100%! It’s a fantastic age difference. 🙂

  4. So I recently met a guy who is part of a group of mutual friends (younger) He must have picked up on my vibe because at some point during the night, he pulled me aside and said “I want to kiss you”, and we laid one on each other. Hot! Red flag. I notice he is obscuring this from his friends, but think hey, it’s new, and I’m into discression, so ok.

    We end up seeing one another the next week. We are on the way to his place and he tells me that he lives with a female roommate and is renting the sofa. He tells me nothing sexual is going on. Ok, this is NY, I have been in a similar situation at some point in life. I’m not going to judge, and until someone give me a reason not to believe them, I’m going to trust and keep my eyes open.

    We go back to his place and fool around a bit. Now, I’m not the type of woman who is going to give a green light signal and then say “I’m just not ready”. I have needs too, and I believe in playing fair. Also, I can’t just “do THE deed” with someone I just met, and I was not going to let on that I was pacing it, so I blamed it on my monthly (which was actually true). We both ended the evening with, ehm, satisfaction, I had to leave early (which was stated beforehand) to greet a guest staying at my house. On the way out, he points out that his roommate has left a wrapped tampon on the table. Red flag.

    I got a nice text from him on the way home. We had been texting one another sweet nothings, and staying in touch via email, but no phone calls from him, and I’m not into chasing a guy. Red flag.

    I’m starting to get the feeling that I’m being put on hold. I am trying leave some space open so I can see him and ask him up about my inkling that he is living with his gf, who he is referring to as his roommate. FInally, I just emailed because while I believe that it’s important and correct to do this in person, I also believe in taking care of things immediately.

    So, I ask if my intuition is correct.

    He replies that I am not wrong, that he had a “special” relatioship with her at one time, but now they are just friends. Also that there are some feeling still there and he is at a complicated time in his life. He tells me that he thinks I’m really special, intelligent, funny and a good person, that he has never felt so good with anyone (as with me, I’m assuming, but no real confirmation), but that he’s not going to lie to me (?) and that he would like to apologize if he hurt me, and he hopes we can still be friends because he likes being around me.

    Hm. Instinct says he’s saying “hey, we can still be friends so I can put you on the back burner in case I need you?” I admited to having been gullible, and told him I was dissapointed that he didn’t come straight out and tell me this, it’s not playing fair and it’s not cool. I also told him that I do like him, and I’m certainely not ready to jump into anything with both feet at the moment, but I did think we had something amazing. (It was!) I also told him he knows me well enough to know that I am not a “back burner” type of woman, and to find me when it gets “uncomplicated”, and left him with a virtual kiss.

    What do you guys think of this? Any additional insights?

    I made a decision to put myself first and let him have room to work out his issues.

    I could use some pointers on this from a guy’s perspective.

    Thanks guys!


  5. @Lynn….We’re totally with you. His whole situation seems fishy, and a bit odd. Not that there’s anything wrong with having a female roommate—we’re totally down with that—but the fact that they once had a relationship AND there are still feelings there is a huge red-flag. Even if they’re no longer “active” it still means he’s hanging around hoping the situation might change, otherwise he would be looking for a new place to live. Also, what’s he do for work? Why is he living on her couch anyway? How young is he? Shouldn’t he have a job, or is he in school? Bottom line: He seems unclear on where he’s at, what he wants, and where he’s going. He seems like a project, one that will require time, energy but maybe not yield the result you’re hoping for. What do you think? Ask as many follow up questions as you’d like.

  6. Hi Guys!

    Thanks for responding.

    He’s 33, an architect. Architects don’t make that much money, but I do think you are right – it’s him that’s haning on to it, and he’s unclear on where he’s at, what he wants and where he is going. In retrospect the couch might be bs. I suppose being honest never got you any skin in that situation, right? Thanks for that insight.

    I cannot take on another project – I have my own life to deal with. My particular conflict at the moment is that I got some feelings sort of stuck in the door. That hurt because I opened myself up to being vulnerable. I’m glad I can still be open, though. I do understand where he is coming from, because I have been there. I hope he finds what ultimately fulfills him because we all deserve that. I do feel that I want to be his friend because of the simple matter that we share some very uncommon life experiences and I find people with whom I can relate on that level very rarely. We can be friends IF we can keep it simple with no pressures and have a blatant honesty policy. I expressed myself fully to him now (including these things I just mentioned), and have no more to say to him on the matter. I’m trying to find some balance between having compassion and my nearly robotic ability to cut people off.

    Am I sending mixed messages? Is it unwise to show this type of compassion? I guess this is the softer side of what I feel, even though everything I have said is true.

    I think because deep down inside if I ask myself honestly I do feel something I would regret not having given a full expression.

    At the moment I feel like I need to go cry and punch a punching bag.

    One thing I do know – no more effort or contact on my part.

  7. Final thought – Do you think that could have been some convoluted play to attempt to get laid? Seems like way too much effort / too risky for that.

  8. @Lynn……We hope this response finds you feeling okay. A good cry, and a few good punches can be cleansing. It’s hard to say at what stage he and his roommate are at with their relationship. The wildcard is the roommate. Who knows how she feels and why she’s allowing him to sleep on her couch. Maybe she considers him a project as well and feels compassion towards him like you do. And how long is she going to allow him to stay there? We think compassion is a good thing, as long as you understand that you’re also attracted to this guy, and our sense is, you hope something will develop over time. (Certainly that’s possible) Meaning, would you want to be friends with this guy if you weren’t attracted to him? Would he still be compelling to you? Since you’re being honest, make sure you’re completely honest with yourself about why you want to be friends with him. And becoming friends with him will automatically make him a project, you do realize that? It’s inevitable. We’d suggest pulling back and seeing if he initiates contact with you. The ball is in his court. One note about architects: You’re right. It’s a tough profession to be in, but many people don’t pursue the actual profession they went to school for. We’re sure he has plenty of marketable skills. A person has to be creative in this very difficult economic time. He’s got a lot of sorting out to do, preferably before you get involved with him, if you do.

  9. @Lynn……What do you mean? When? His initial meeting with you? Here’s a quote from one of the writers on our Relationship Memoirs page that might answer your question. “If a guy wants to have sex with you he’ll say anything, do anything, act nicer, be more compassionate, reach out to your friends, compliment your mother, and even suck up to your father to get what he wants.”

  10. Thank you. I have to take an honest look at that and what I want for MYSELF. Yes, I am attracted to him but do I want a project to work on other than myself? Hell. No.

  11. Ahhhh.. and here’s some perspective. He has or had been getting pressured to get married.


  12. DEAR GUYS,
    So ive been working at my job for almost a year and im the only girl there as a waitress so all the guys are good friends with me except for this one guy who is the cutest of them all hes a year younger than me im 20 and hes 19. I guess hes always had a crush on me and never told me cause he was afraid cause at that time i had been dating my ex bf so after me and my ex had recently broke up 2 months back he finnaly got the courage and told his buddies to tell me that he liked me and tried to hook us up keeping in my the guys also told me he was a virgin. So after all that i finnaly gave in and went over to his place and we hooked up i caught feelings for him and all the guys say he has too but the problem is he only texts me when its the night before our day off and the rest of the week he dosent it didnt really bother me hencing we see each other everyday at work but the problem is he told all the guys after the second time we hooked up what we had done and i told him not to do such thing and he did with me knowing and i over heard so after i over heard this i started ignoring him strongly i asked him what he wanted me as and he just responds that he will be anything i want him to be for me and so i asked him do u want to be friends with benifits and he said ok not understanding hencing i took his virginity so after i explainded to him he said no not at all he said we can be friends and then he was like i dont know i mean i dont understand what he wants nobody dose he dosnt have a girl friend he works sleeps and plays soccer thats about it he dosnt even check out other girls when im around unless if im ignoring him like now he dose it infront of me during break to see if he can get a reaction i dont know if he want just to be friends with benifits or be together i just dont understand and its like i have to explain why im mad for him to be comfortable agian like what can i do besides talk to him or ignore him to get him to talk to me first cause if he want to be friends with benifitis im ok with that compleatly as long i get a response im good i cant do this mind reading thing all he dose is stare at me when im not looking n when i glance his way he arches his brows and acts like hes mad like what is his problem … I really need help i dont know if i should stay with him as what ever we are or drop him and move on with my life please help…

  13. @Anita….This sounds confusing. Honestly, FWB never really works out. And he seems very wishy washy about what he wants. We see only more confusion and hurt feelings here. We say move on. If he’s not mature enough to tell you what he wants and feels, then you need to find someone who is. The ball is in his court. Stop making it easy for him.

  14. Hi Guys! I’m back!! Would you believe I’ve found a guy who is wonderful, available, and doesn’t play head games? He’s 12 years younger than me (I’m 52; he’s 40), has a 12-year-old daughter from a previous relationship, and found me online. He said he messaged me several times with no response; he didn’t want to give up on me. Well…after some time we connected. I couldn’t believe that he was even real…it just all seemed too good to be true. It’s been 2.5 months, and already we are bf/gf (at our age?) with no regrets. I’ve totally played things cool (and with “The Guys'” help feel like I could write a book on what NOT to do), and he shocked me with a comment of “marry me eventually?” the other day. He talks of us as “we” and is absolutely amazing. I’ve never had trouble getting dates and am told I look much younger than my age, so I’ve dated the hot, wealthy guys and have found them shallow, at best. This guy is average, not wealthy, honest, caring and sincere…that makes him a total hottie to me. You guys have always been honest with me about some not-so-flattering decisions I’ve made in the past, so I wanted to let you know that time paid off for me…and so did your worthwhile advice. Now, off to donate to the cause!!!!!! Big hugs to you all!!!!!

  15. @Breezy…….So great to hear from you. And to hear you’re doing well. We wish you the best!!

  16. whathappenedwas // November 30, 2013 at 10:14 am //

    Hi Guys!

    Well, yes, you are right. Younger guys aren’t in it for the long haul, but… I’ve been seeing this guy for quite a while. He chased me until… and now, it’s so complicated. He’s young, married a short time, no children. I am Mrs. Robinson! Now, he tells me that he wants a divorce from his wife but waiting until after the Holidays. Wants us to cool it so we don’t get caught. When I “cooled it”, he said that’s not what he meant and was hurt and mad. Now he’s just mad and is having a hard time with his feelings. We’ve decided to go back to friends but I know I can’t do that. Yes, I want to be with him longer, this is a real relationship, he’s a great guy. I’m not unrealistic as I know, he’s in his 30’s, he won’t be with me always. But for now he’s the best thing that has happened to me. What do I do next? How can I reassure him that I was/am in this for the haul.

  17. Hahaaa! You guys crack me up. So true, dating a younger guy is a waste of time, unless a time waster is what you’re looking for. My rule is, if they are younger and DON’T have kids, then beware because they may try and coerce you into having kids – I’ve had that happen, or they are looking for the hot mom fantasy.

  18. @Jen……Well, the Hot Mom fantasy is certainly a universal one amongst guys. In fact, just put HOT in front of most things and it works. Like Hot Grandma for instance. 🙂 Thanks for sharing your perspective.

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