New date concerns

Personally I think you have done exactly the right thing the fact that you were out of your comfort zone on so many levels is massive The fact that so soon in the relationship (or meeting) you already knew he drinks every day means he must have brought that up and that would have my stomach telling me to watch out
I think you were very brave to be so definite in your mind, knowing me I would have gone on and on and regretted it Well done strong lady

Bless you, that must have been hard, but I think you right FWIW.

Plenty more people out there, you only need one to click with?

Good luck

Big thanks to everyone who posted to this thread yesterday.
Last night I had a phone conversation with this man and explained that it just didn't feel right on quite a few levels.
I really struggled with actually saying out loud that I didn't want to see him again.
In fact I think if it continued I would definitely fall for him.
There was a vulnerability and complexity that seemed to draw me in. Even more worrying was that his personality reminded me of someone I had fallen for 20 years ago.
I now recognise this, but had the most dreadful nights sleep trying to rationalise it in my head.
Possibly the fact that I'm recently retired means that I have lost my daytime structure a bit and have more time to dwell on things.
But thanks to all, as reading the posts helped me to make the decision yesterday and space, plus disengagement, is what is needed.

Beware of the alcohol - "he likes a drink most days" may mean exactly what it says, or not.

How long have you been chatting before your 2 dates?

What do you mean opposites "looks wise"?

If you are having fun can't you continue to have fun?
You don't need to go away together unless you want to.
Meals out, concerts, cinema, a trip to another town for the day. All the kinds of things those without a partner, miss.
Be open with him. Tell him you aren't ready for a full on relationship.

I think you are very brave. Dating online or dating in the dark as I call it. I am too comfortable to even try dating. I use my time raising funds for the village. Maybe I am just happy in my own company. The above posters are all correct. Look out for the red flags

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.

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.

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.

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)

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.

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.

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.

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

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!

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.

Proof not prof.

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.

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 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.

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 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.

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.

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?