Late last year my sister-in-law set me up with someone. We corresponded by email for a while then decided to meet for a mid-afternoon coffee. We duly met and chatted for an hour or so. One thing of relevance is that she said she makes judgements quite quickly. I enjoyed her company so rang her that evening suggesting going out for a meal. She broke down in tears and said no. We’ve not made contact since, though she did ask after me to my sister in law sometime later. When I related this to my brother a few weeks ago, he said, “That sounds like a ‘Yes’”, and my SIL has been encouraging me to make contact again. Apparently she’s still unattached. I’m somewhat leery as she did say no and I’ve no wish to be seen as a stalker. And besides, if she did mean yes, then I’ve really no wish to pursue something with someone who’s manipulative. If she were interested in me, all she has to do is email or ring me.
But then I’m a 46 year old virgin who’s clueless about women.
She doesn’t sound like stable, enjoyable girlfriend material. Sounds more like a person w/ unresolved issues. If the hour you spoke after emailing didn’t show some spark between you, at least enough to suggest a future plan then and there, these are not the droids you’re looking for.
I’m actually going to go against the grain, and suggest one more try. Sounds like something was definitely up for her that day, and you have no idea what. Your SIL encouraging you to reach out again makes me think she may have had some conversation(s) with this woman that contained encouraging information. Of course, you could always ask her.
If I’d been having a bad day and started crying for completely unrelated reasons when a guy asked me out, I’d be mortified. I would be so embarrassed, I wouldn’t reach out to him again, even if I was interested.
What’s the worst that could happen? Either she says no again and you drop it forever, or she says yes and you get to know her a little better and find out she’s bad news and you drop her, or she says yes and you have a great time and maybe more.
It’s not like she’s a great close friend you’re going to lose as a friend if you ask again. It’s a woman you barely know. Go for it.
ya whynot, what have you got to lose? you’re 46, you’re overthinking things. if you’re really uncomfortable, perhaps your SIL could act as a go-between again?
What kind of feedback did you get from your SIL? Did this woman flat out tell her she’d like you to contact her again? When this woman asked about you, what did she specifically say to your SIL? If she was embarrassed and regretful about crying and spurning your advances then give it another shot. Or better yet, SIL should tell her to call you this time. If not, then let it go.
1 - I love the advice/user name combo by WhyNot
2 - If you ARE leaning towards reconnecting, have the SIL ask and clear up why she melted down over the phone like that. It’s shrieking violins if a woman in her late 30’s-40’s has an emotion overreaction like that.
Ask SIL if she has specifically indicated that she would like to hear from you again. Maybe your SIL just has this crazy dream of her friend and you going out and her life will be complete, who knows. Basically, sometimes people just imagine two people together because it will be fun for their life, and they’re really looking at the situation realistically.
This was Crazy Sign Number One. Two strikes and you’re out. Sometimes people have a bad day and just feel emotional and overwhelmed. Maybe there was some specific thing going on that day. All that is fine and it would be sad if you never gave her another shot. But maybe she is crazy. Any more crazy signs and you run and don’t look back. And tell SIL to stop setting you up with crazies.
How much do you want to go out with her again? You said you enjoyed her company the first time, but that’s not exactly head-over-heels. While you’re weighing all the other advice, trying to figure out whether “no” meant “yes”, give a little thought to what you want, too.
So be friends. If you enjoyed her company, tell her that.
Do you want to see her again? Ask her why she broke down in tears when you called. I really think that the direct approach is best. You’re adults. Maybe you’ll get some answers. Maybe not. Right now you have no answers.
