New date concerns

I sounds like you’ve already done them. You have your gut instincts which shouldn’t be ignored. I have zero experience of this sort of thing, but this sounds wrong to me, and feel it does to you too.

Don’t accept second best, there are loads of people out there.

All the best.

Well this isn’t for the long term, is it? Too many no nos.

But no reason why you shouldn’t have a bit of fun for a while. It won’t do you any harm to shake it up a bit. And then you can go back to your quieter life when you want.

Have some fun and don’t commit to anything more than some nice days out. Make sure he’s knows that’s how it is

Be careful and take things slowly. He seems to be going much too fast and I felt uncomfortable just reading your post.

You dictate the speed at which this goes. Don’t be pressurised into making longer term plans, holidays and such. Enjoy his company on dates. Only do what you feel comfortable with.

Listen very carefully to what he says. The clues are often there as to whether there’s any future. He is already ringing your alarm bells.

IME men do this a lot, go completely over the top (and be aware that he may be playing the field and doing exactly the same with others), fall in and out of love at the drop of a hat. They can be exhausting … and then they cool off just as quickly or want to change you.

The age difference doesn’t have to be a thing. It can make a lot of sense to date younger men for all kinds of practical reasons so long as you have things in common. It can be good too to meet people from other walks of life so long as, if the relationship has legs, they don’t start expecting you to change to fit their life rather than find compromise.

Slowly, slowly …

This sounds highly risky you don’t have too much on common AND you only have what he says as a guide to his character.
If you have a comfortable life with your own house don’t mess it up, be very sure he is all he says he is. When you have had a couple of nice days out go away for the weekend with him, if that goes well then there is a chance of a lasting relationship.

faringdon59 Congrats for going online dating which has really worked for a close friend but I'm a scaredy cat...what/where did you go for your two dates ??coffee or a walk ..just asking as you say he likes a drink most days and wondering it this is on your mind?

If you enjoy his company, keep enjoying it. Just don't give in to pressure to do anything you don't want to.

Some people TALK about a possible future together when really they're no more certain than you are. They're just words.

Might get a bit more difficult if you start to fall for him.

There are worse things than being alone. Being in a bad relationship is one of them, so be wary.

I think I would listen to my instincts. When I was working, a police woman from the City of London Police came to the solicitors firm I worked in and gave us some advice re keeping safe. Aside from practical advice, I thought her most valuable piece of advice was: if you feel uncomfortable or edgy about somebody, listen to those feelings and avoid that person.

I’ve never seen an online dating site but ‘lonely hearts’ ads from men almost invariably ask to meet someone ten years younger! So I’d already be a bit suspicious. If the talk turns to money/borrowing money (even the smallest amount), walk away. Tbh I’d have walked away already but I can see the reasons you might not. Enjoy your dates but don’t let loneliness rule over common sense.

I would research social media. See if he has a Facebook account etc. Definitely keep your hand on your money.
You enjoy his company but take it slowly. Be careful not to share too much personal information.
You have said that you haven't had a relationship for eight years. Combine this with the last eighteen months it is not surprising that you are feeling a little jittery. Be careful and you really have nothing to lose.

Does he have the same core values as you, faringdon? I would be wary of the fact that his drinking habits are the complete opposite of yours for a start.

Listen to your gut instincts - the gut is known as the "2nd brain" - those instincts are there for a reason. He makes you feel "nervous" - then you feel better when he presumably charms you during the date. That sounds like bad news.

There will be someone more suitable in time .....

I would try googling his name, see if he is mentioned on his employer’s website, see if he’s on Facebook. This all assumes he has given you his correct name. Do you have any prof he is who he says he is?

I have no experience of online dating but I find it strange that a man of 44 would be interested in a woman of 66 - again assuming you’ve both been honest about your ages - especially if you have little or nothing in common. Also you say that looks wise you are polar opposites, which I take to mean he’s good looking and you don’t consider you are, or you wouldn’t have mentioned it. So another question as to why he seems so keen (I don’t wish to offend you, but a lot of men go initially for visual attraction).

Trust your gut feeling above all else. He may be genuine but he may be after your money. We’ve all read plenty of stories about men like that, who swindle women out of thousands. In a worst case scenario he may be even more evil than that - I’m sure I don’t have to spell it out.

In your position I would be very wary.

Proof not prof.

If I were you I’d nip this in the bud before you fall head over heals. Your gut is telling you beware and most of the time gut instincts are right. Move on to someone more appropriate.

You are uncomfortable for a reason.
Mentioning going in vacations so early in the relationship is a red flag to me.
You barely met him!

I would talk to him and you want to take it slower.
His reaction will take you everything.

Nothing strange in older woman /younger man.Age is or so said but a number . Not wishing to blow my own trumpet, since widowed.experienced the same.I did the thanks but no thanks Early days.

I hate being so cynical but who has paid on your dates? Does he seem solvent? Does he work? Does he put you out of your comfort zone in a good way or does he just make you feel uncomfortable? Have fun but take care.

He would be 54 not 44. Why should a younger man not like a older woman?
Listen to your gut feeling, enjoy his company, do not give out personnel information, and only do what you are comfortable with.
If it gets too uncomfortable, stop seeing him, but opposites do attract and he might like like you as you are.

Listen to your gut feelings faringdon59 but you don't have to commit to a long term relationship. Sometimes it's good to get out of a rut or comfort zone and be a bit adventurous. Enjoy time with this man and have fun. I met my husband via an advert in the paper pre Internet and we couldn't be happier.

Keep looking, sorry to say he seems like a shcmoozer.

Differences may seem exciting to start with, but I think some common ground is needed somewhere.
Promises, promises, holidays, days out etc. Looks like he's telling you what you want to hear.

Why does he want to hang out with someone who doesn't drink etc. Do you want to hang out with an alcoholic?

'6 years either way' goes the saying. (obviously, there will be exceptions)

Not had any experience myself but alarm bells are ringing as you yourself feel uncomfortable and he is talking about holidays on the second date. That seems too quick to me and I’d be wary. As others have said, we have all read stories of women like you who have been led up the garden path and relieved of savings and peace of mind. He may be perfectly genuine but….what do you know about his relationship history? That’s the best place to start I think.

The minute he asks you to pay, has forgotten his wallet, needs you to buy something because he’s short of funds, run a mile!
Your gut is your second brain. Listen to your gut.

My fabulous OH is 53 and I will soon be 67. We met through an online dating site and did take it quite slowly but we have been together almost 17 and a half years now and we are both extremely happy.
At the moment he is busy laying a patio in the garden at the back (at least I hope it's a patio! ). I was married before but he has never been married, although had a long-term relationship. I have two adult children and two grandsons. He has nieces and nephews and a great-niece and nephew. We have a lovely blended family of all ages including his 94 yr old father. We are in the North of England and they are in the South, but we do see each other quite regularly (Covid did put a stop to it for a year, but it's now resumed again).
I'd say take it carefully and slowly, but it can work out and enjoy yourself. I'd agree with being careful with finances as well! Good luck.