How Should An Older Man Deal With A Flirty Younger Woman?

Let’s say you have a friend, he’s in his late thirties. There’s a gal in your sphere; she’s eighteen years old and she’s a terrible (or terrific) flirt. She flirts with everyone including your friend.

It seems obvious to you she’s looking for love and approval from a father figure and you sympathize but you are not close enough to her to do much. Plus you’re a woman!

But then your friend confides in you, he has sexual interest in her that he could act on. Would this make you uncomfortable?

How would you handle this and can you match your response to your chart?

42 thoughts on “How Should An Older Man Deal With A Flirty Younger Woman?”

  1. Yeah would make me uncomfortable and i’d tell him he’s having a mid life crisis and to stop being such a nonce. That he’s old enough to be her father and how would he feel about a near 40 year old man coming onto his innocent, if provocative, offspring.

    But then she is an adult and men do look at 18yr olds on porn sites and what not so if thats her choice. But yeah i would definitely try to dissuade him.

    Venus in aries would be quite blunt, stellium in virgo hold the moral high ground, pisces rising, sag mc, let em get on with it if they both want the experience. Man i shoulda been a libra, i just cant decide!

    I was accused of flirting with a couple of 20 year olds last night (i’m 38) but they were funny and the thought of a relationship with either never once crossed my mind. I do like younger men but not that young. What dyou have in common? Your friend just wants to feel young flesh if you ask me.

  2. Just for the record… this is a real situation but I am not the one it. The scenario belongs to a friend of mine.

  3. Avatar
    Melody Zindell

    I think this one is a little tricky…since black and white has never been my m.o., and I would love to show how certain tendencies are reflected in the chart:

    My Venus Opposite Saturn: Venus Saturn aspects often show up in intergenerational relationships, and I’ve had a couple and don’t gasp in horror when I see them. My son Damian’s father is 13 years younger than I and before that I dated briefly someone 15 years younger. (I was also married for 18 years and completely on my own for the last 8, so I just haven’t had that many relationships.)

    I assume that Saturn in the 7th house or possibly Libra would reflect the intergenerational thing as well.

    My youngest sister married the athletic coach of her high school when she was 18 and he 38. It was the scandal of the town and they had to leave, but although the marriage has had its challenges, they are still together and solid.

    In their case, he has his Moon in Capricorn in the 7th house, and was probably the one first attracted to her. She was/is vibrant, athletic (Olympic vollyball team) beautiful, and a huge flirt, even at 18. She was also sexually molested by her brother for years and definately needed both security and escape which she got from this marriage. It has been really good for her. Her chart is intense and clearly shows the trauma and need for love.

    On the other hand, you have to know that it is difficult from a life experience etc. point of view…may be some maturity issues somewhere on the part of the older person.

    My Neptune in Libra in the 8th house: pretty much can go anywhere relative to staying open and unconditional…

  4. It wouldn’t make me uncomfortable, but if I were friends with both parties, I would explain to each of them separately what I know. Not gossip, just laying it out, such as “hey dude, you should know, if you don’t, that she’s a great girl but she does flirt with everyone, just so you know.” “hey girl, he might have some stuff in common with your father which might be good or bad, just something i noticed.” I feel like that’s being a good friend.

    But then, I would be hands off, because what business is it of mine? Maybe the relationship will work, maybe it won’t, but either way they might learn something, it might be a very necessary experience for one or both of them.

    The only time it would make me uncomfortable would be:

    1)If either one of them were married or in other relationships, it would probably make me not want to hang around them anymore, because that doesn’t jive with my personal values, or

    2)If it went sour and one of them started complaining all the time but not doing anything about it (Aries moon, complain but after that take action or you’ve lost me).

    Other than that, I think accept your friends or don’t be friends with them. It’s not my job to map out the trajectory of their lives – I leave that up to the universe.

  5. If his interest is just sexual, then he needs to just stop right there because then what? The girl is going to feel used afterwards (because she was!). If that’s his only motive, then I would say something to him, and leave it at that.

    Don’t know if I can match it to my chart, Venus/Uranus in Scorpio, Mercury/MC/Mars in Sag, Pluto in the 7th in Libra, Pisces rising.

    I remember myself at 18/19/20 and how goddamn stupid I was regarding men/sex and how many times I fell for it.

  6. my inclination is to stand back and get out of the way. let the lava land where it may. why should i get burned in the process?

    young people frequently fall for people much older than themselves. when i was in my late teens and early twenties if a person was not in their thirties i didn’t give them a passing glance. of course i live to regret that stance.

    if the guy friend has a S.O. then he and i need to talk. we’re friends so we can do “talk” right?
    that is about as much as i would be prepared to do since neither of the two parties, it seems, is asking for my opinion or suggestion.

    and btw if either or both of them keep acting out or stating libidinous oohs and ahhs about each other to me i’m going to tell them to quit doing that and face one another. i don’t like it when folk attempt to direct their sexing for someone else through me. i admit it might be a venus conjunct pluto thing that i have with this.

  7. I would just step back and be there as a listening board in case either of them needed it. I don’t claim to have the answers to life (made too many mistakes) or relationships and believe that we’re all where we need to be at any given point in time. Scorp. rising with Sag. Neptune/Jupiter conjunct. Libra Sun/Venus/Uranus in 11th. Cap. Moon. Saturn Gemini in 7th.

  8. I’m a real life example of that. My last relationship was with a 41-year-old. (I’m 24). I’ve never dated older men before, neither was I attracted to them, but this one….boy the attraction was so heave I threw all caution to the wind. I was the one that made the first move.He on the other hand was clear from the beggining that he didnt want a relationship with me and was constantly telling me “not to fall in love with him.” So, of course I did! It was tough getting over him, but I dont regret one bit. He wasn’t my sugar daddy, or a father figure but ceritainly more mature and settled in both his oppinion and life. If this guy you know is upfront about his intentions for casual sex, then it’s no different than any other situation with any other guy she might meet. It’s all about fair-play, mutual consent and respect.

  9. Oh and I am a Virgo Sun, Moon, and Venus and Gemini rising. I dont know what to look for in the chart about older men…Elsa you have my chart, so I’m sure you can see it. Maybe Pluto in 5th house?

  10. Unless asked specifically for my views I wouldn’t offer them.

    The age difference wouldn’t bother me particularly if the word “love” had been involved. I think the keywords here are “flirt” in her case, and “sexual interest” in his. The idea that she is seeking a father figure may be inaccurate, if she’s a born flirt, that’s all it may be – pure flirtation. She may need to learn a wee lesson, he may need one too, for he’ll no doubt be left in the lurch if his “sexual interest” develops into something else.

    Reasons from my own chart – hmmmm- not sure. Capricorn on the descendant, Mercury close by – not afraid of age-gap relationships (I had one for 33 years). Aquarius Sun – like freedom to follow my own inspirations, and allow others to do the same.

  11. It’s not the age difference that is disturbing to me: it is that she is 18 and he is in his late 30s. I hooked up with my partner when I was 24 and he was 42. It still works. However, if I was 18 and he was 36? Forget it. He would not have liked me, nor I him. When you’re 18, you’re barely out of your childhood home.

    But! I still cannot judge. Hop to it, if that’s what you desire, but never stop questioning the social implications of that attraction.

    I do have 7th house Saturn, which apparently often leads to having an older partner or late marriage. My partner has it too. So I got the older partner and he has the late marriage. Whatever–it works. But it NEVER would have worked while I was, essentially, still a child. And an 18 year old might be legally in his sexual league, but you can’t convince me it is a relationship based on mutuality–which for me is paramount to it’s success.

  12. I have Venus square Saturn, but I’m still not too cool and froody with the whole May-December thing. (I’ve been burnt! My 8-years-older ex said he’d NEVER date young again after me, and now that I’m his age then I understand completely.)

    I think I’d just say to him that he’d be using her for sex and she’s young and would probably get more attached than him and then she would end up miserable and he’d be doing it to her. But then he’d probably screw her (and screw her UP) anyway in the end, and I’d walk off disgusted.

    Incidentally, Gene Weingarten’s chat this week featured a poll on what people think when they see May-December relationships. Some folks may find this interesting to read:

  13. I’d advise against it, but I’m not going to stick my nose too far in. People are gonna do what they want to do and I don’t think anyone else can protect them from it — it’s how they learn, right? This girl could learn a lot from this situation (hopefully “Don’t do it again”).

    Venus in Virgo, Aquarius Rising.

  14. It wouldn’t bother me necesserily. Or if it did bother me it wouldn’t be just because of the age difference.

    Someone can look at that and think’oh how unhealthy’ but provided both people get what they want out of this and it makes them happy, who are we to stand in their way?

    It would bother me if I thought he was just going for a shag and she was deeply deeply attached to him because that could get ugly real fast.

    But if they both seem reasonable, and honest with one another – why not?

  15. I have a 7th house Saturn so my partners have always been older (Waves to kashmiri). If the man was my friend I’d tell him straightly and bluntly that she is too young for him and try talk him out of it. (I have venus in aries, 6th house) Of course men always have sexual interest in younger girls, don’t they? I don’t think there’s anything odd about this. The thing is, he has the choice not to act on his sexual interests. The girl is too young to know better… she may not act responsibly. He may want sex; she may want more; or vice versa. (not that it would be her fault for not knowing what she wants, she’s just too young to know at 18)

    wow, do I sound like a prude? seriously if my 30-something year old male friend were to hook up with a 18-year old girl – I’d ask questions and say my piece but I wouldn’t stop him. It’s his life!

  16. I wouldn’t say anything, but I would definitely question the guy’s motive.

    I’ve got Venus/Saturn all over my chart and of course the older man thing happened to me when I was younger. Almost every time I remember feeling attracted to the guy’s experience and the feeling of safety and security it gave me, not the actual person himself. I liked the fact that I was likable to someone of his stature; it made me feel legitimate or something. And the guy? Sometimes it was sexual interest, sometimes more emotional – midlife crisis, a need to “teach” someone younger, feel better about himself and getting older. I remember one particularly intense experience (pluto transit to venus, what else) where he and I were immediately attracted to each other upon first sight. He was my mentor, and 25 years older. Completely inappropriate. Obvious power dynamics involved. And I’m glad I stayed far, far away from it. First time I felt that kind of attraction for another person and I will never forget it – it was powerful. But the situation was all wrong. My venus/saturn couldn’t abide by anything ‘inappropriate’ and put the brakes on despite my deep attraction. I’m sure glad for that, as it kept me out of trouble! Would have ruined my life and his.

  17. If he’s a friend? I’d tell him to stop being a perv and leave her to guys her own age. And if he felt all “Oh I am older and established and have so much to offer her” I’d remind him that unless he’s Donald Trump she’s not going to be interested for long.
    I’ve also got Saturn in the 7th, and I am WAY over the big age difference thing.
    She is unsophisticated emotionally in terms of love realtionships, he is not; he has an awareness that she does not and so sorry, no matter how flirty she is he should show some restraint.

  18. Considering he is my age and she is the age of my oldest child, yes, it would make me uncomfortable.

    Libra can see the appeal on both sides but it grosses her out. I would approach her first carrying a LOT of Saturn and let her know that while this kind of thing can be fun and the attention she will get from it..probably exhilarating that she is worth so much more than being someone’s fling or mere sexual interest. I was this way at 18, but I believe 37 woulda been outta my age range then. That’s OOOOOOLD to an 18 yr old. Does she have any idea about his interest?

    Then I’d leave it alone. If he asked, I’d remind him I have kids that age and if it were my daughter I’d be all over him like white on rice. But she isnt..but she is someones..and leave it at that.

    They are both adults and if they are looking for an exciting fling..whatever, not my business.

    I gotta give all this to Libra. Merc in Scorp could dig into the details and figure out the right way to approach but Libra is so repulsed it would be hard to remain objective and of course my Virgo Venus just wants to help all involved but again..trumped by Libra Mars

  19. If either of them asked my opinion, I’d give it: back away, fast! Having made some amazingly bad choices both at 18 AND in my late 30’s, I’d feel qualified. But people have to make their own choices & hopefully learn from them, either good or bad. I don’t listen to unsolicited advice & don’t offer it either.

  20. My friend was once the 18 year old and she meet this 36 year old. Yes they had chemistry but ultimately she got hurt as she found out that she was just a conquest.

    She looks back at it now and realises that she was searching for her father, as her father was not there emotionally.

    What happened to him, he got married to a woman (in her 30s) and had lots of babies.

    I also have to say she repeated the pattern a few times over and the same ending kept on occuring. He would marry a age appropriate woman. But now she has met a man who is now age appropriate to her.

    So yes, this does not sit well with me at all, as I know the outcome.

  21. I would be honest and tell him that he is too old for her. It won’t make any difference becaues he won’t believe me.

    It must be my virgo moon.

  22. looks like from the original comments this post is about 4 years old . . .

    so she’s in her 20’s now and he in his 40’s—–how’d it all end up?

    (and i wouldn’t assume it’s the 18 year old that is necessarily gonna get burned.)

  23. i’d not be shocked, but i’d ask him what kind of maturity he was looking for. whether he really wanted to go through the teen years again from so close a perspective. whether he was comfortable being a “daddy.”
    and i’d wonder whether he felt threatened by a woman who could hold her own against him.

    i’ve seen these things play out from time to time. generally the mature men get tired pretty quick. and the ones who get stuck on 18/19 year olds and keep looking for newer models tend to have serious women issues.
    one of the reasons i avoided older men at that age. the ones that went after me tended to have problems.

  24. I’ve got cappy moon, venus conjunct saturn and 7th house cusp in cappy, so it’s doubleful that he’d be confiding in me. If he was, he’s looking for the responsible answer which is that he’s an adult and should act like it (by not pursuing this).

    This is a tough question, given that no situation is ever black/white. Also, given that there are many details that we are not privy to. That being said, to me, the age difference here matters, because it’s a sexual interest on both parts. She’s a young adult and I can’t imagine that sexually or emotionally, she’s ready for something serious or more involved than a sexual experience (that’s totally a judgement call on my part and may or may not be true). Now if both parties were interested in pursuing a long term relationship (leaving sexuality out of it till sometime in the future when they know one another better) I’d see that differently,

  25. I have a friend doing this right now. He really doesn’t want to get married or have kids, but he has a career and owns his own home. I think he went for a younger gal (she’s 21) because she’s still in party mode and he doesn’t want the things many women his own age want.

    I have said nothing. Other friends have already said it anyway and it’s not like he’s listening. He’s not my boyfriend so fuck it.

  26. I would def say something , if it is appropriate or not, I don’t think I could keep my mouth shut!

    Probably nothing to her, as I imagine a 18 year old being very impressionable(?), and that is what I would use as argument to him too.

    I would tell him to stop thinking about himself. Even if she would be satisfied in a relationship with him, thinking she is happy, lucky whatever. What reference point is he giving her?. He would be stealing her youth! That is the major reason I am againts major age diffrence in relationships. One is bound to have to muture beyond their age ,and allthough it can be good ,serious is for most of life,some years should remain untouched.

    I strongly opposed to my brother dating a 16 year old when he was 19. I told him it can easely become psychologicly damaging to her.

  27. So I’m a cap rising,with a libra sun, and an absolutely packed eighth house and what I would tell him is that he has to realize he has tremendous responsibility for the welfare of that girl and his handling of the situation. Shes eighteen, eighteen is not 24 — a girl that age does not have a brain yet.

    I’d tell him as a father figure his job is to make sure she can sort out her feelings and come out still being able to trust the world. If he is going to have sex with her, he had better be prepared to take care of her emotionally or acting on the impulse would be a violation of her he would later regret. I’d also say that I doubted he was truly attracted to her and more surprised she is attracted to him. However it’s unlikely she is attracted in a way that’s truly appealing. At that age, they want attention and are experimenting with their bodies and do not have much consciousness attached to emotional hygiene. So if hes willing to be an experimental subject she will later write about on Twitter, he should go for it.

    I’d say he had a chance to affect this girls life for better or worse and he’ll probably like himself better later if he is not an asshole.

  28. I was never a party girl, and at that age, I was just as wary of being used to for sex as I am now. I would probably tell the guy he should back off – especially if he was only interested in sex – but as I said, I never did sleep around. I just wasn’t interested in that.

    My sister is involved with a man over twenty years older than her, and they became involved when she was twenty/twenty-one and very shy/agoraphobic (just like me). They met over the internet, and have been involved for fourteen years now. I know of another woman who’s married to a man with only a difference of a year or two in the age gap between them, from the potential couple you mention above. They’ve been together for a long time, since she was in her early twenties, and are over the moon happy, but she had a good head on her shoulders, as well, and he was wild about her from day one.

  29. In my friend’s case, I don’t think he’s using her for sex. She has moved in with him and he lets her run the house. He’d never gone out with a gal NOT his age before, so I don’t think he’s some pervert. His last two girlfriends were very much “we’re getting married or we’re breaking up.” I don’t imagine the relationship lasting if this gal decides she wants to be a mother.

  30. That’s a HUGE age gap, they can’t possibly have anything in common. At 18, most girls don’t know what they want, and she could change between then and the next five years. I guess if the 37 year old doesn’t mind playing daddy and the 18 year old doesn’t mind being a trophy.

  31. I’m with Lilly… live & let live. They could both learn a lot from this. Find me a relationship that dosn’t have a disaster element woven into it?

  32. Avatar
    Stellium in Taurus

    I’d tell him, “No, you are delusional. Bad idea, really bad idea. She’s far too young for you. If you do this you might really hurt her then I’d be pissed and I would not be able to look at you the same way.” I have kids that age, and I have friends with kids that age. That really grosses me out to imagine that happening to them.

    I don’t know about the planetary stuff…. let’s see, maybe Saturn sextile Sun/Mars?

  33. i would probably give him my honest assessment of the situation but leave it up to him. virgo + sag. if she were my friend, maybe a different story.

  34. I agree with Lilly “live and let live” (Aquarius rising, Venus conjunct Uranus). Sex has a different meaning for different people, and also in different cultures. It depends on the case, sometimes the older one gets burned while the younger leaves like nothing happened. From my experience I can say Venus-Uranus moves on 🙂

  35. “But then your friend confides in you, he has sexual interest in her that he could act on. Would this make you uncomfortable? ”

    I would most definitely tell him to be a grown up here! Point out that while 18-year-old is of age (at least where I live), she is in a very different place than he is, and that could make things complicated. Not mention anything of what I know of all this to the girl. I guess this is my Capricorn Moon in the 5 house, mainly, but yes, I also have a loose Venus square Saturn.

    BTW, a friend of my SO briefly dated someone graduating from high school two years ago. He was 35, she should have been 18-19. To their credit, both SO and his group of friends thought it was weird, and let their friend know. He is now living with a woman in her early 30’s, who I felt slightly intimidated by when I first met her, because she just seemed perfect, but learned to like a lot during a weekend trip.

  36. Avatar
    Stellium in Taurus

    The more I thought about this, the more upset I felt. I have a dear friend who has a daughter fitting this description VERY well. We raised our kids together and I’ve known this kid since she was in her mother’s tummy.

    If I had a 37 year old FRIEND who confided that he was seriously considering a sexual encounter with this girl I’d be livid. I’m Aqua rising too plus I have uranus in the 7th but I truly do not believe that live and let live applies here. This guy is acting like a predator. Just because she’s 18 does not mean it’s OK. So he does it with this girl, then the next time it’s a 17 year old who catches his attention. See where I’m going with this? If he opens that door he’s truly going down the wrong path. If he likes younger women then he should raise the bar and find one at least in her late 20s. Makes me wonder if the guy in the example has already done this with other teenagers.

    If this man was a truly a FRIEND as the example states, then no way would I condone his behavior. I would tell him bluntly that I thought he was really off track. Thankfully I do not believe any of my male friends would do such a thing.

    Sorry to you other Aqua rising gals here, I know I can sometimes be very strong in my opinions and I may have sounded offensive. I don’t mean to offend …. I am often a live and let live person too, but I hope you can understand that by interjecting my friend’s daughter into the equation really made me see how much I would hate to see her get used by a guy 20 years her senior. I just cannot see it going anywhere good and I felt a sense of protection for her. I think that as a culture we trivilize encounters like this but the reality is that things can, and do, go wrong. What if she got pregnant? What if she got really hurt? Plus I cannot have any respect for a man who is so clearly ruled by his penis. I hope this makes my position clear.

    Merc conj Mars conj Sun (daisy chain) plus Saturn sextile Mars/Sun (forceful communication about old fashioned values). Maybe Pluto trine Merc too (diagnostic skills).

  37. *high fives stelliumintaurus*

    I’d call him a perverted hog who can’t think with his mind,only his penis and he better make sure his computer is clean because the visual difference from a 16 year old to an 18 isn’t that great.My sister runs with people a bit younger than her (shes 25) and the majority of them would not have anything to offer a grown man(which,granted,can be exceedingly immature) besides the use of their body.All they pretty much want to do is drink,party,be skinny and hot,update their facebook,make thier bf’s jealous(if they have them) and eff like there is no tomorrow,throw on some more drinking a dieting and “sexy pictures and that is the portrait of a fair part our female youth.

    The young lady may just be a product of our society where physical attractiveness and outrageous sexuality is the norm and is also the only way a young woman can feel validated(is via men wanting her).Not that that is an excuse to act loose.I’d tell her she best to be careful about who she’s flirting with unless she wants to have a whole lot of regret later on.I know how flirting (especially without forewarning like” I’m a flirtatious person but I don’t mean anything naughty by it”) can get you in a situation you didn’t see yourself in (been there) ,then there is either acquiescing out of some misguided sense of empathy or hurt feelings on the flirt-ees end.Some chicks are just teases though and don’t care whos hopes they get up and consequently let down.They just see it as power or something?I don’t know for sure.

    So I digressed a bit again,and it’s all kinda harsh.I have a sun/merc/venus in Libra conjunction in the 6th/dsc.Saturn cnj Pluto In Libra conjunct in the 7th.I’m an Aries rising with Mars in Sag in the 8th,I certainly know about powerful drives but wrong is wrong,my own life experience colors my opinion as well.

  38. Biologically, I would offer perspective of natural fertility aptitude is desirable . Perfectly natural. My partner is 12 years older than myself. My n. node is in the 6th and I gravitate to polished skillsets to apply to my capacity to learn and apply in service. There is a hell of a lot of work to do and babies are needed.

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top