Flirty v desperate: Another stupid dating dilemma

April 8, 2016 4:07 PM

This is such a trifling thing, but I keep going round and round about whether to reach out to this guy and have come to the tribunal of Ask to render a decision. Multiple choice answer key inside.

So: Guy's from far away. He was in my town on business, came to an event I was at to say hello to a friend, we hit it off, ended up getting a drink together after the event broke up and talking for a couple hours. I was attracted, he seemed to be too, but nothing happened and I had sort of sighed and written it off as a pleasant evening.

But I saw him again that weekend, though, when I came to a thing his friend had invited me to. Ended up being just the three of us; we were never alone, but we talked more, and it was just a really fun day. We had both dropped hints about wanting to see each other again --- I mentioned a trip I was planning on making to his area and he volunteered to show me around, as we were saying goodbye he said he'd be back up this way in a month or two and said we should hang out again. He didn't ask for my number, though.

As it happened, my trip out his way is off. I hemmed and hawed a bit but reached out to him via social media, mentioned that I wouldn't be in his area after all and said I found myself disappointed I wouldn't see him again. I then gave him my personal email and said he could reach me there if he wanted to continue talking.

He wrote back the next day, a brief, mildly flirty message saying he was sorry to miss me in person but was glad to have gotten my email address. I replied the following morning, again brief, chatty, and I hope mildly flirty. Since then, silence. It's been nearly a week.

So, as I see it my choices are:

A) try emailing him again
B) wait a few weeks until he's headed back in my direction then try emailing him again, so there's a chance I can see him again in person
C) accept that it is 2016, he has seen the last email I sent, he knows how to type, and I should just let this go.

I feel like such a tool. It's C, isn't it? This is so dumb. It's just...it's a rare thing for me to feel such a strong, immediate sense of attraction when meeting someone, and that part of me keeps hoping against hope.

posted by maggiepolitt to Human Relations (15 answers total)

B. Outside work, there is nobody including my close family and friends that I keep up a back and forth every couple of days email thing with and in a busy week, I can easily forget to email someone back.
posted by AnnaRat at 4:13 PM on April 8, 2016 [2 favorites]

D)

wait a few weeks until he's headed back in my direction then try emailing him again, so there's a chance I can see him again in person say yes if he reaches out then to get together.

It was on you to contact him about going to his town. Likewise it's on him to contact you when he's coming to your town.
posted by headnsouth at 4:23 PM on April 8, 2016 [9 favorites]

B + invite him to a specific thing at a specific day/time. Not "Let's hang out" but instead "Would you like to meet for a drink on Tuesday evening?"
posted by BlahLaLa at 4:29 PM on April 8, 2016 [4 favorites]

B. He's generally given you positive signals. There's not much point to A because you don't have much to talk about until you see each other again, since you don't really know each other. C is pointlessly pessimistic; what is there to lose in reaching out again when he's coming back to town? Even on the off chance he thinks you sound desperate, there's no harm in that, and I can think of a number of reasons why he'd welcome that but not write back to you now.
posted by metasarah at 4:29 PM on April 8, 2016 [1 favorite]

E) Accept that it is 2016 and when you meet people under weird circumstances, you have zero idea what is preventing them from emailing back. Send him another email and say "Hey, no clue what this silence means, and if you are just not into me, okay. But if you have been tied up due to weird circumstances that you can't explain to a person you barely know, I really enjoyed meeting you and I am really hoping to hear back. So do not hesitate to drop me a line when you can."

Or words to that effect.
posted by Michele in California at 4:32 PM on April 8, 2016

The signals I'm getting are, this guy is attracted to you, he'd be up for some NSA fun but he's not looking for a relationship. If the possibility of that would hurt, I would not reach out to him again.
posted by ThePinkSuperhero at 4:39 PM on April 8, 2016 [2 favorites]

D) ... wait a few weeks until he's headed back in my direction then ... say yes if he reaches out then to get together.

That.

This is a variant of the Brad Pitt / Angelina Jolie Rule going on here. If he's into you, he'll reach out. If you're into him, you say yes. Until that time, just keep being awesome.
posted by Cool Papa Bell at 4:42 PM on April 8, 2016 [2 favorites]

D) wait a few weeks until he's headed back in my direction then say yes if he reaches out then to get together.

This one.

Send him another email and say "Hey, no clue what this silence means, and if you are just not into me, okay. But if you have been tied up due to weird circumstances that you can't explain to a person you barely know, I really enjoyed meeting you and I am really hoping to hear back. So do not hesitate to drop me a line when you can."

I would definitely not send this. You guys have only met once. It sucks, but that's how these things go. Asking why he's not contacting you implies there's an expectation for him to contact you, and based on the brevity of your interaction no such expectation should exist.
posted by Anonymous at 4:56 PM on April 8, 2016

I know it can be scary, but there is a lot of value in being direct. So another option would be a brief email saying that you will likely be in his town on X date and would he like to meet up then, and to let you know if he will be visiting your area before then. That puts the ball completely in his court without having to guess about incomplete flirty email chains or other hints, and from how he answers I think you have a lot more information about his potential interest.
posted by Dip Flash at 5:09 PM on April 8, 2016

Definitely B. Who knows why he hasn't emailed you back? Maybe he is anxious about making a bad impression. Maybe his dog died. Maybe he is playing mind games. Maybe he doesn't want anything more to do with you. Either way, you don't know and you really have little to lose (and much to potentially gain) by reaching out to him.

Of course, he may well reach out to you first!
posted by ssg at 5:43 PM on April 8, 2016

I vote for option B, if you want. If he's heading to town, he may email you, as well - who knows?

I'd like to mention that, as a potential reason for no communication for days, he might not want to continue daily emails with you, and if that's the case, it may have no bearing as to whether he likes you or not.
posted by destructive cactus at 6:05 PM on April 8, 2016

Feels like you have nothing to lose by going with (b), as long as it is at least a couple of weeks/corresponding with the time he said he'd be in your town. With a reasonable pause, you won't look weirdly overinvested, so the worst that is likely to happen is that he's not interested and tells you so/doesn't respond. Best case, he wasn't sure whether you were interested at all, and when you contact him, he'll know you were.
posted by praemunire at 6:52 PM on April 8, 2016

I think you should leave the ball in his court because:

A. He's not interested in a relationship with you at this time for whatever reason.

Or

B. He doesn't feel comfortable communicating enough to arrange a meeting with you.

Let him show you that neither a or b are true by waiting to hear from him. You don't want to be with any guy without a and b. There are other fish in the sea. Just keep rocking on with your life and be happily surprised if you hear from him again.
posted by Kalmya at 7:33 PM on April 8, 2016 [1 favorite]

There is no requirement that he contact you. But you have big feels for him and are spending too much time and energy on this. Contacting him to find out if he even got the email and to try to make sure this doesn't turn into a situation where both of you feel it is on the other person to make the next move or whatever does risk the possibility that he will react negatively and make it clear that he thinks it is completely unreasonable for you to inquire as to what the status is and whether or not you can expect to hear back.

To me, that is a feature of this approach, not a bug. If someone thinks being considerate and having clear communication are ridiculous expectations, I want to know that sooner rather than later so I can write him off and stop pining for him. I don't want to leave the door open to a relationship where he is trying to be too cool to care like a 13 year old. It isn't like you are trying to pick out engagement rings. Asking if he is just busy and letting him know you are hoping to hear from him should not be a big damn deal. And if it is, I feel I am better off knowing up front that he thinks leaving me hanging is acceptable behavior. That is not a precedent I want to set this early in the relationship.

Yes, lots of people act like I am being unreasonable. I don't spend the next week agonizing over them. I get on with talking with the folks who don't have a problem trying to clearly communicate with me about where we stand and whether or not I can expect to hear from them again.

To me, the right answer here is not based on whether or not I am guessing the most acceptable solution in his eyes that will keep the door open as long as possible. To me, the right answer is the one that answers the question as to how he plans to treat me in the future and whether or not that is treatment I want more of. And if the answer is "Honey, I am just not that into you." that gives me closure and that works for me.

Best of luck.
posted by Michele in California at 10:31 AM on April 9, 2016 [2 favorites]

I think definitely B -- or email again after a while if/when you have a specific thing you'd like to tell him. Like "I finally saw that movie you were talking about and you were absolutely right about the mis-casting of Robin Williams!"

A lot of people (maybe introvert-ish like me) find it very difficult to keep up an frequent correspondence with someone... it has WAY more to do with the demands of the mode of communication than my degree of interest in them.

Absent doing an activity together, or years of shared experience, it may be hard to sustain a conversation mediated by email or social media. I wouldn't take that as a slight - he's expressed interest in you already. Just wait until he's coming back to make some plans or reach out in a way that is really about sharing some thing you wanted to share - not about expected communication.
posted by pantarei70 at 12:11 PM on April 9, 2016 [1 favorite]