Dating advice - too aggressive or interested?

[Lolailo]

I would like to get some advice for the following situation.

I am not sure how much context to add, but I have been single for 5+ years. I haven't dated much dealing with other things life threw at me.

I am kids free for two weeks and last night I decided to do something I enjoy and I joined a meetup of a "bowling" group. I'm quite good at bowling and have played for many years. A man approached me (very friendly) asking about my game and we chated briefly. We met again while ordering at the bar and I mentioned a friend of mine during our conversation, to which he asked me if she was cute. I told him yes and that she was single. Then he asked me "what about you?".

I deflected and brushed it off without answering his question, and then he insisted in paying for me beer. I thanked him saying I should pay next time, to which he responded he hoped so, because it meant he would see me again.

He asked for my social media, and when the competition was done we stayed to hang out and play some more (as so did a lot other people). He also tried to "stay in touch professionally". I don't want to be outing, but let's say that if I was a baker he asked me if he could order a custom cake from me.

He has added me in social media today and sent me a message that I haven't opened yet.

I find him very attractive physically and intellectually. But I thought he was a bit young. In looking at his socials he is at least 30 for sure, but I think he is JUST 30. I'm 40.

I would like to get to know him (we share a hobby and he is as good as me and was really fun to play) BUT if he keeps being so straightforward:

A. Friendzone him
B. "What about you? Are you single?"

Get to know who he really is through joined activities through time. He has made an impression but you don't know him well enough yet for either A or B

If a man was 40, he wouldn't care about his potential partner being 30, so you don't have to feel intimidated by that.

Update: I opened the message. He says it was lovely to meet me and asks for info about a meetup I am going next week. He wants to come 😁

(During our conversation he asked me if I would come bowling next week and I said I am going to another meetup related to my work and invited him, to find people for his "custom cake").

The age thing... I have usually dated men around 10 years older than me. But at 30, I don't feel like a craddle robber, I would be open to getting to know the person. He is independent (immigrated by himself, just like me), has a job...
I guess it is more about ME being rejected.

And about options A and B... his message was perfect. I understand he is interested and putting some effort 😁😁 But if he is so direct again asking me if I am single (or similar), I need to say something! My previous answer was "let's not go there". So he doesn't really know if I am single.

Hi @Lolailo i love it when a guy is just direct instead of going round in circles. For me the confidence makes him more attractive. Some guys give eye contact and then nothing or wait for the woman to say something, so annoying.
Enjoy getting to know him! Yay! 😊

I think he's probably figured out with are single.

YOU are

His being direct by asking if you are single

Surely, You just say Yes or No ?

God I prefer direct, why not hey. He obviously likes you and wants to get to know you a bit more. You find him attractive and it’s up to him if he wants to date an older lady. I wouldn’t rule out someone 10yrs younger or 10yrs older than me.

He's just being direct and showing interest, doesn't sound aggressive to me. Have fun!

It seems ok for a start but I'd say be cautious as he seems very comfortable chatting you up and moving quite fast which could me he does this regularly. I guess it depends what you might want out of it. As it's been five years and you've been dealing with other life challenges you probably do need to protect yourself a bit. Are you thinking a no strings fling could be good? Watch out for love bombing just in case! A bowling buddy could be fun at minimum then you can have a chance to get to know him properly. Good luck!

ps. I think someone asking you if you're single the first time they meet you at a social event is quite full on.

I don't think it's full on, it would be rude and uncomfortable to try to pursue her/get to know her if she has a partner.
I agree with the points about taking it slow and not rushing OP as he might be a chat up pro. Keep an open mind about what it could turn out to be, but even hobby company could be good

I replied with the info about the event and we have exchanged a few messages.

He was flirting hard. I told him I liked his sense of humour. He answered "I like you. I mean, your sense of humour. I am just messing around" that threw me off a bit. Now I don't know if it is just banter and he is a flirt.

But the ice is broken. We will meet at the event and I will be there with a friend so I feel comfortable.

Being straightforward and direct is good, but it can also be more subtle. There is some enjoyment in guessing (looks, eagerness to meet, asking for my number) rather than been so blunt. We only met once, organically, that is different from connecting online, texting and going on a date.

You are way overthinking this.

He clearly likes you and made his interest very clear.

It sounds like you fancy him as well.

You appear to be both single.

You have mutual hobbies and interests.

Not seeing a problem.

Good luck, OP.

I am not looking for casual. And I have gotten too comfortable being single. I don't need a man. But I would love to find a man who makes worth it spending my energy on and risking heartbreak. Haven't found any after my divorce.

I am also a slow burner, so having the hobby is ideal to get to know each other without expectations. And at worst, I have a bowling buddy.

My fear is that he seems too comfortable chatting me up, as you said. So was there a connection or he does this every week?

About love bombing, thanks this forum I learnt a lot and I am alert. My XH love bombed me. He is a narcissist, I didn't even know that term until I found mumsnet. But I have learnt so much here.

I have gone through my Facebook and saw that I still had photos with my ex and the "got engaged" and "got married" events. Maybe I should say something. Hopefully he doesn't think I am still married (divorced 5+ years, I just didnt want to remove all the photos when we divorced)

I like people who aren’t ague and are clear about what they want and their intentions. There’s absolutely no reason why you can’t just take your time getting to know him socially and just see what develops.

He asked you if your friend was cute before flirting with you? Eh...wtf. sorry but...he's a player. He couldn't have made that any clearer.

If hes cute then treat it as a bit of fun. Just don't trust him as far as you could throw him.

Sorry typo, should have said I like people who aren’t VAGUE. (Irony 😅)

If you like him, be open to taking it further.

However, if he's an attractive 30 year old
man who's confidently asking after your friend before turning his attention to you, be beware that there's a very good chance he's a player.

Tbh thinking on it, it could be worse. He could be the negging sort - asking if your friend was attractive because he thinks having friends who are better looking than us is a source of insecurity for women.

I mean, lets face it - why else would you ask a random woman if her friends are attractive? Its clearly meant as either - 'I don't fancy you but could you set me up with your attractive friend' (player) or 'I want you to think I don't fancy you and compare yourself unfavorably with said friend, so that your self esteem takes a hit' (negging). Either way, he's not a nice human being.

Don't let little things like that slide. They are the sort of neon red flashing flags we brush off in the beginning. Taking them as 'misunderstandings'. Because we are normal, nice people and we assume that baseline for others. Especially if they are flirting with us. But he has already shown himself for who he is. His subsequent followups aren't much better by the sounds of things if they make you feel thrown off balance and unclear as to his intentions.

Just, keep your eyes open going into this op.
Keep in mind that good people make us feel secure about their intentions. They don't blow hot and cold. They don't make hs feel like we are chasing. Or like we should put them on a pedestal. Watch out for red flags like that.

He’s a player, no doubt about that.
If you want casual / quick thing, go for it, but don’t expect him to be serious.
It’s very clear what his about.
Also, if you have only been with men your age/older, just a warning: men his age have a lot of demands and expectations when it comes to sex, often they don’t even ask, they just do it.
Just so that you know.

I understood the friend comment as "I'm letting you know I am single/looking". That's why I mentioned she was single. Once I said that, he turned it around to me fast.

He is confident, no doubt. Not convencionally attractive, just my type. But not the type women would throw themselves at in a bar. So I don't know how much of a pickup artist he may be. I mean, he is handsome, but there were many men who were HANDSOME, tall and buff. One of them with an accent that was so hot 😍😍😍

Don't be too quick to settle with him given that there was other male talent bowling also - wise not to cut out other possibilities yet. He does appear to be a bit on the prowl which would put me off. You seem to brush off his question about your mate being cute, but that there shows that he's on the alert and after every opportunity - if it was an attempt to show he's single, it was at best a clumsy one and makes him come across as desperate or creepy tbh.

“ mentioned a friend of mine during our conversation, to which he asked me if she was cute. I told him yes and that she was single. Then he asked me "what about you?".”

That would be my first Flag. Player vibes.

I don’t know if “aggressive” is the right word but too pushy/forward too soon, too sure of himself.

Personally I wouldn’t pursue anything and just enjoy the bowling hobby. But I’ve been played by a player before and him being so straightforward was (with hindsight) a major sign which I ignored because I was lapping up the attention/compliments/smooth talk, so I might be projecting my mistrust for anyone who trots out similar patter.

Are you posting on here because your internal radar is telling you something is “off” about this? Maybe it seems a little too good to be true?

Proceed with caution.

@DatingDinosaur I have reflected on it today and I believe I crave attention/connection so a bit of excitement becomes the highlight of my week. I start fantasizing about a perfect relationship, when reality is I know little about the man to even decide if I am interested in him.

I'm very inexperienced in dating, and I found the interaction novel. My gut told me ONS, hence my avoidant response. But the rest of the afternoon and subsequent messages made me think differently. We shall see if he comes to my meetup on Wed, by himself.

I must confess I have gone through his social media. No trace of gf but he lives with two female roommates who are friends since primary school. He doesn't follow any bikini pictures account 🤣 but he follows women excelling in intellectual fields. I have also seen group photos from his uni years where other men put arms around girls, but he keeps his hands to himself. He looks very driven and intelligent. I ratified that I like his sense of humour. Friends comment he is socially awkward.