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I'm growing uncomfortable with his questions! Should I go meet him for coffee?

Tagged as: Dating, Flirting, Health, Online dating<< Previous question   Next question >>
Question - (9 November 2017) 12 Answers - (Newest, 13 November 2017)
A female United Kingdom age 36-40, *annah B writes:

Dear Cupid,

I met a 41 year old guy who describes himself as sophisticated, also wants a sophisticated lady, online.He writes he is ready for a new relationship. He writes he has never been married, has no children and lives alone. He has a Bachelor degree, a software engineer. I am completing my PhD and also put that I was ready for a new relationship. I have also never been married with no children. He contacted me first and we have been chatting for four days now. On the first day, I told him I have a physical disability due to past polio and move with a crutch. He said that wasn't a problem and I should not worry about it. He says I am very pretty (My profile pic has only one face photo). I told him no.He sent me his number the first time but I only text him back on my phone yesterday. The questions were basic get to know.

I feel like he has been getting weird by the day. Less know-you chats and yesterday he started making jokes which allude to sex. He said another facial photo of me on watsap was so pretty he could kiss me! I tactfully avoided the them. Then he went on to ask if I wear high heels or prefer flat shoes. I told him I prefer flat shoes. I told him I was curious why he asked me that. He said he just wanted to know.He also asked if I have a car - I said no. This morning at 9:00 am he sent me a message and asked if I like long boots. And that's because he has a soft spot for women with wearing long boots. He had asked me for coffee next week but I said I could make it the following week and he is fine with it. I am confused because I thought he was a nice guy and that I would finally meet someone and have a a relationship but now I feel I am getting uncomfortable with his questions. I may not go for the coffee.

And to add, I have no problems wearing long boots at all. I actually love them. My concern is why is he telling me to wear them when we are meeting for the first time over coffee? Why does he want to know if I have a car?

Please advise. Thanks.

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A female reader, femmenoir Australia +, writes (13 November 2017):

femmenoir agony auntThis guy isn't interested in pursuing a "proper" relationship with you and all the signs are right in front of you.

This guy, he's got a few favourite fetishes up his sleeve and he wants to use YOU to make his fetishes come true.

He's tapped into your weaknesses and to date, he's been using it in his favour.

You should "test him", pretend to be into something weird or nasty and ask him, would you also like me to wear my long boots and coat and nothing underneath, or my shortest leather mini or my leather neck choker when we meet?

These are just crazy examples, but you get the picture and then you'll know exactly the type of guy he is by his reply.

If he's smart though, he may be onto you and he may say, no, i'm not into that stuff, only the long boots.

Either way, i would not encourage you to waste your time meeting this guy, as he definitely isn't looking for what you are looking for.

He professes to be a "sophisticated" guy, but his behaviour and language spells otherwise and who knows if he's really as well educated as he's making out to be.

Everything about him spells WEIRD and i think he has this grand and delusional view of himself.

You can do so much better and yes, the real gentleman are still out there, because i met and married one of them.

Good luck!

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A female reader, aunt honesty Ireland +, writes (13 November 2017):

aunt honesty agony auntHi OP follow your gut instinct and don't meet up with him. Talking to you like this after four days really is a big huge red flag. I know if this was me personally I would not meet up with him I would feel to uncomfortable. I had the same experience years ago and well you just need to listen to your gut feeling when something doesn't feel right.

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A female reader, YouWish United States + , writes (10 November 2017):

YouWish agony auntOh God. Unfortunately, you just attracted one of THOSE.

This guy isn't looking for a relationship. He's looking for a fetish accessory, and he's thinking that because you are disabled, that you're desperate to be this accessory.

What guy describes HIMSELF as "sophisticated", yet within DAYS, he abandons all semblance of sophistication and drags the gutter with sex and fetish and Long Boots? REALLY??

I'll say this -- I have a soft spot for guys with foot fetishes, but breaking out the boots and sex talk from the get-go is extremely off-putting.

You're worth far more than that! Hell, if a polio survivor was the mother of Michael Jackson and the Jackson 5, not to mention President of the United States, you can do far better than being a fetish accessory! You're about to become DOCTOR HANNAH B for crying out loud! You didn't sign up to be DOCTOR FETISH ACCESSORY.

If you didn't need your crutch, I'd advise you to ram it up his ass. But that would be a waste of a perfectly good crutch!!

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A female reader, anonymous, writes (10 November 2017):

Don't meet him.

Have nothing more to do with him.

He reminds me of the guy who I was talking to over the phone - who I never met in person - but was set up with. I was supposed to go out with him on a first date. He asked me if I like to wear garter belts and spiked heels!! And then went on about other bondage type accessories. Really??? Yes, it's true! The "friend" who set me up wasn't my friend for long and my interactions with this pervert ceased immediately!

You can tell by his questions where his interests lie. He is looking for sex. And he is trying to lure you in gently hoping you won't notice that fact! But you are a wise and perceptive woman. Sadly for him!

Forget about him.

He sounds like a total loser.

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A female reader, Youcannotbeserious United Kingdom + , writes (9 November 2017):

Youcannotbeserious agony auntReminds me of a guy I communicated with many years ago (long before on line dating, when you replied to box numbers from adverts in papers). Got writing to this guy who started off ok then got a bit weird, asking similar things to this guy you are chatting to. We had arranged to meet up but I decided to call it off and got a very abusive letter back from him, telling me he had made all sorts of plans and how I had screwed him over and what a slapper I was. Close call!

If you don't feel comfortable, then PLEASE listen to your gut instinct and call it off. I hope you haven't given him any personal details like where you live or work so that you can shake him off easily.

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A male reader, Billy Bathgate United States + , writes (9 November 2017):

If a guy is creeping you out online do not meet him in person.

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A male reader, anonymous, writes (9 November 2017):

Franky looking for partners online is totally unacceptable to me. Online is full of liers and weirdos who lie about everything including their gender. I still believe in the old fashion way of meeting others in public or social places like at work or college or at a dance. Especially it is important that someone has to see that you are handicapped upfront and accept it before starting to flirt or to become special.

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A male reader, BrownWolf Canada +, writes (9 November 2017):

BrownWolf agony auntHi OP,

Do you not see the warning sign???

Let's flip this around and use yourself. Do you see yourself a sophisticated woman, with a bachelor's degree, and not having a chance to be married, have kids, and surrounded by good things??

If you were all that and live alone...then two things...You like living alone so you can have sex whenever you want and with whoever, without having to commit to anyone.


You have serious issues in your life, and people don't want to be around you.

The fact that sex was already brought up....which kind of guy do you think he is?

Use your sophisticated self and get him out of your life. All I see is a dumbass trying to make himself seem important.

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A female reader, Honeypie United States + , writes (9 November 2017):

Honeypie agony auntI think the fact that he is trying to turn it sexual SO soon is a bit of a red flag.

The whole high heels and boots... it's just an odd subjects.

If you feel a bit weirded out, I'd listen to that gut instinct and not take it further.

Asking you if you have a car might be down to WHERE you can meet up. As in doesn't it HAVE to be near a train station/bus stop or... do you have a car? See what I mean?

Apart from sexual stuff, I don't see any really weird things here - but YOU are the one conversing and if YOU feel uncomfortable... then don't go further.

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A male reader, N91 United Kingdom + , writes (9 November 2017):

N91 agony auntAvoid definitley.

Going into his sexual thoughts/fetishes after 4 days? No thanks.

You already know it's weird, don't ignore that feeling.

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A female reader, mystiquek United States + , writes (9 November 2017):

mystiquek agony auntHe definitely has his preferences and he's stating of them quite early. I don't blame you for being uncomfortable. I would be too. I wouldn't meet him. If your radar is sending off the "danger danger"...listen to it!

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A male reader, Denizen United Kingdom +, writes (9 November 2017):

Denizen agony auntSounds as if he is drifting into the weird part of the spectrum. I personally would listen to my gut reaction and drop this one back into his muddy puddle.

You could always test him by asking if he likes something more outré - whatever you like to invent. Then you reply that you definitely do not, and at that point you have your definitive answer.

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