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Inexperienced with dating and unsure about seeing an older man

18 replies

TheMintTraybake · 29/09/2026 19:49

So I’m 24, went on one date last year, never kissed a man, not had sex, held hands nothing, just that date but it was more friends hanging out. So I’m very inexperienced when it comes to men. I think because I’ve gone so long without it that the idea of being vulnerable and opening up to man, being affectionate is foreign to me and feels weird. I’ve spoken to a few guys but nothing serious, I just get awkward and make some sarcastic comments because I’m scared to show any real emotions lol.

So with my job, there’s a supervisor that works with some of the other employees who are lent to our business of a community employment basis. My current manager actually left the workplace and worked alongside him before returning back to our current job so she does not like him, she worked below him and since he’s younger I sensed it was to do with jealousy. So she really hates him for personal reasons.

Sinxe he sometimes visits us at work to check on his employees, I’ve spoken to him a few times. He is a very gorgeous man and has beautiful eyes, only thing is that he is 35. He doesn’t live far from me so he waves when he’s passes me on the roads. Last week he added me as a friend and starting chatting. He let me know he enjoys going to my workplace because he gets to talk to me and has asked me to meet him, go for a walk and has asked me out on a date when I’m free. I’ve made up some excuses saying oh I’m busy and I’ll need a new job if we’re seen together. The thing is from the moment I met him I’ve had feelings for him but now that I’ve gotten to know him they’re even stronger. I don’t drink and neither does he, this is always something I’ve looked for in guys and the reason I don’t talk to guys my age because all they do is go out and drink. He has his own home, has a great job and his own business, he offered to drive 4 hours at 11pm to pick me up from the airport and to bring me dinner at work when I was working until 2:30am. He seems like a really great guy and I really like him but I’m so scared because I’m not used to this, I’m inexperienced and awkward and shy but we do have feeling for each other. I’ve also never mentioned men to my family so even if I was to meet him I have no idea what to say or how to tell my parents I’m going to meet a 35 year old man who they have heard of through my job and he works not far from my father so he knows of him. I’m really looking for advice on wtf to do as my heads all over the place, I don’t want to lead him on because of my avoidant attachment.

OP posts:
mcmooberry · 29/09/2026 19:52

I think 24 and 35 is fine, I would advise you go on a date with him.

inerja · 29/09/2026 19:56

The power imbalance is wrong.
you also shouldn’t shit where you eat.
get another job first at least

VoltaireMittyDream · 29/09/2026 20:01

It’s not the age difference, it’s the power differential (his seniority at work), your inexperience, his love bombing and a sense I get that you are quite emotionally young for your age.

Unless I’ve misunderstood, you are not living a fully independent adult life - you’re worried about what you’d say to your parents about dating, etc. I’d proceed with caution and bear in mind that men who zero in on women who are inexperienced / naive / insecure and sweep them off their feet almost never have straightforward motives.

Funkyfoxy · 29/09/2026 20:36

Yh this is off. He has sensed your vulnerability and wants to sleep with you and will dump you. Men have a radar for this. Don't do it.

AutumnLeaves5 · 29/09/2026 20:49

I used to work with someone like that. He’d target younger/more junior employees (especially vulnerable ones), show them interest, be supportive, flatter them, find things in common and it was all just an ego boost for him. It never meant anything. He’d change roles and start the process all over again. Your boss probably hates him as she can see right through him and his behavior.

Be patient, it’s not avoidant attachment, it’s your intuition screaming at you that he’s not someone you want to get involved with. I didn’t meet my boyfriend (same age) until my 30’s and I was inexperienced but I’ve never once felt awkward with him or been intimidated by his experience. I never really enjoyed dating and, didn’t want meaningless relationships, so for me it was worth waiting for someone that was perfect for me and I felt proud to introduce to my family.

bookshelf85 · 29/09/2026 20:51

get some therapy then when you’re better in yourself date and he’s a red flag walking

ScorpionLioness79 · 29/09/2026 21:07

The offer of driving four hours to pick you up and bring you food at 2:30 a.m. would be normal behavior for an established, exclusive couple--not somebody you've never even been on a date with. Your lack of life experience has you seeing this as positive versus the alarming negative it actually is.

I'd be firm with him and tell him you won't be dating anyone you work with. Since you're looking to date, I suggest looking into Meetup.com groups and getting a new hobby men gravitate to. In that way, you can gradually get to know a guy first, rather than the quickness of OLD, which you'd likely not be comfortable with.

We all have firsts in our lives, like a first job, a first date, a first relationship, which can bring on nerves. But with time and repetition, it becomes more comfortable. You're no different than anyone else dating for the first time. Mostly everybody has some nerves at the beginning, but avoiding your goal will have you living in a lonely bubble, since you say you'd like to date.

Instead of a fear, think of it as a challenge and a means to achieve your goal.

If that guy at work is so attractive, so career successful, so charming, so kind, then why doesn't he already have a gf or wife? Probably because he doesn't want to put in the effort that requires. But brief casual flings require very little effort for what will be a big payout for him, and a rude awakening for his unsuspecting prey.

Goatsarebest · 29/09/2026 22:07

I agree with every bit of advice on this thread given to you OP. Please take it on board.

FloralHut · 29/09/2026 22:35

ScorpionLioness79 · 29/09/2026 21:07

The offer of driving four hours to pick you up and bring you food at 2:30 a.m. would be normal behavior for an established, exclusive couple--not somebody you've never even been on a date with. Your lack of life experience has you seeing this as positive versus the alarming negative it actually is.

I'd be firm with him and tell him you won't be dating anyone you work with. Since you're looking to date, I suggest looking into Meetup.com groups and getting a new hobby men gravitate to. In that way, you can gradually get to know a guy first, rather than the quickness of OLD, which you'd likely not be comfortable with.

We all have firsts in our lives, like a first job, a first date, a first relationship, which can bring on nerves. But with time and repetition, it becomes more comfortable. You're no different than anyone else dating for the first time. Mostly everybody has some nerves at the beginning, but avoiding your goal will have you living in a lonely bubble, since you say you'd like to date.

Instead of a fear, think of it as a challenge and a means to achieve your goal.

If that guy at work is so attractive, so career successful, so charming, so kind, then why doesn't he already have a gf or wife? Probably because he doesn't want to put in the effort that requires. But brief casual flings require very little effort for what will be a big payout for him, and a rude awakening for his unsuspecting prey.

Edited

Exactly this.

Most 35 year old men who are genuine and available for a relationship and have some money are snapped up as soon as they're slightly single.

There's probably some red flags that you can't spot but a more experienced woman would. He probably is more impressive than men your age as he can drive/has money/his own place.

My top tip for building more dating experience would be to try to find a mixed group of friends (male and female) and just socialise with them regularly.

Not dating or connected to work. It can be hard as a lot of hobby groups are full of old people but there'll be some "spaces" in your town where the younger folk go.

Just get used to communicating with men as new friends, seeing them regularly. No dates or intensity.

Keep things simple and cheap - pub, walks, house hangouts etc.

People at the same level as you who are starting in life or studying and might not have much money and/or be living at home.

Stay with a group your age. Stop worrying about talking 1-1 to men as if you're saying something right or wrong. It's just chat, or you can sit with the group and be quiet.

Morecoffeeneedef · 29/09/2026 23:11

Your older colleague 'hates' this man. Does she speak and act like someone who is jealous or are there other reasons? He doesn't sound a good bet for you, though the age gap in itself is OK in my view.

fuschiaproudparrot · 30/09/2026 04:52

Do you belong to a culture where you have not been exposed to many men ?

Yello24 · 30/09/2026 05:16

It sounds as though you are ready to try a relationship and sex and you are attracted to him. He will have the confidence and experience and maturity that men your age might not have and that might suit you BUT you are so inexperienced that you may not have the mental strength to deal with the potential risks of this one.

Overall I’d agree with others that it’s the workplace relationship that makes this one too risky. And the fact he’s pursuing you so strongly is dodgy.

I had similar at about 22 with a 36 year old boss. It was fun for a while but he did turn out to be an absolute shit.

24 with no experience is fine anyway. Very usual. I have children your age and there are very many who haven’t had a proper relationship yet. You sound a bit pressurised by this man so that in itself is enough to tell him to back off.

Mysticguru · 30/09/2026 08:29

Don't!! You are going to get hurt. Be patient, the right one will come along. NEVER have sex with someone that is your superior at work for a multitude of reasons.

watchingthishtread · 30/09/2026 08:44

The one other woman in your story (who happens to be older than him so presumably a bit more experienced in life) hates him. Don't dismiss her feelings as jealously. Of all the women I know who have ever taken a dislike to a man, jealously has never been the reason. Find out more.

Disturbia81 · 30/09/2026 08:46

That age difference is creepy.

Denim12 · 19/10/2026 06:23

Disturbia81 · 30/09/2026 08:46

That age difference is creepy.

no its not

crunchycrackers · 19/10/2026 18:20

I think OP, you sound similar to me in my early 20s also zero experience and I finally asked a guy out at work who was same age and we dated for 6 months. I wasn’t sure how I was going to initiate a kiss (I felt like it was long overdue and turns out he was a bit keen lol we had met for coffee and then we were standing and talking and he leaned forward - thank goodness I wouldn’t have done that myself).

I wasn’t ready for sex with him I enjoyed making out and was ready for the next relationship after that one.

I think this guy may have expectations but that’s normal and up to you to decide if that’s how it goes. Just be prepared for the work environment to be a bit awkward if it doesn’t work out. If it’s a casual job it’s easier probably but if it’s your bread and butter I’d maybe look elsewhere for a relationship.

(BTW after a few fun dating experiences I ended up meeting my DH and we have been together for 20 years so I am happy to say it worked out eventually and I hope the same for you, OP).

BeenThereBackThen · 19/10/2026 18:49

So the other female who hates him worked with him being the manager and probably got to observe his behaviour up close. It is very likely this is why she hates him. Not because he is younger and more senior but because he perhaps was showing the same attention to females below him and picked up on his slimy-ness. Why did she leave? Perhaps he was the reason, who knows.

I’d not get involved with this person if i were you, pretty eyes and own house are no guarrantee that you won’t get hurt.

Funny he wants to bring you food in the middle of the night, my money is he is a slimey bastard who simply wants to take advantage of you.

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