Is there such a thing as a second chance in online dating?
March 21, 2013 7:06 AM   Subscribe

We've already met. I messed it up (kinda), and now I want to ask him out again. Yes, I know: optimistic.

Me: female, nearly-40, been doing online dating for 3 months.

Him: male, 41, the nicest guy I've met either online or IRL, for quite some time.

This happened about 5-6 weeks ago. He contacted me, we went on one date, to a bar on a Saturday night. We both got really drunk (happy drunk, not sloppy drunk), had an awesome time, talked and laughed for 5 hours until the bar closed. The chemistry was awesome, and he made a few comments that made it clear he was....into me. He also sent me a nice text when I got home. He then went away for work for a week, I texted him once, he never replied. About a week after that, I messaged him via the dating website to say hi and, that I was a little embarrassed about how drunk I was on the date, but it was nice to meet him. To my surprise, he replied with a lengthy (and lovely) message about what a good time he had.

Okay, so at this point we have someone who's being polite because he's a nice guy, but is not interested in pursuing anything. I get it. However, since then, we have messaged back and forth maybe...5 times each? And, uh, quite a few things have come out. He has said, in as many words, that:

- he thinks I'm funny, attractive and smart
- he also thinks I am looking for hot rich guys, I'm only doing online dating for a bit of a laugh, and that I am only into short-term relationships (SO freaking embarrassing and NOT TRUE. It kills me to admit it, but once the memories started coming back...I think I was in liquored-up, who-gives-a-damn, good-time-flirt mode on the night, and took it a little far. It's a defensive, ego-driven thing, and something I'm working on.)

The conundrum: I want to ask him out on a second date. I think he likes me, but does not want to date me because he thinks I'm not looking for a genuine, long-term relationship. I understand that I could be completely wrong about this. I fully realize that he may have other reasons for not suggesting a second date, and that there is an 80 - 90% chance that he will say no, and I am prepared for that. BUT I really like him, I have nothing to lose, and I want to reach out to him one more time before dropping communication altogether. I'd rather be rejected for who I am, than for who I pretend to be when my defences are up.

My question is: how the heck do I word this? Do I send my usual jokey message and throw in a 'Hey, howsabout another date?' at the end? (Seems dumb, after so many weeks.) Do I be straight up about the fact that I wasn't my true self on the date, that I put on a bit of an act when I'm nervous? Basically, I want to be honest, without wanting to come on too heavy and serious, but without slipping back into the flippancy that got me into this position in the first place. :(

(Also: I listened to Brene Brown's TED talk on vulnerability, like 5 times. I want to do that: be vulnerable, but in a good way. I've realized that I have zero clue how. This is a long-term issue that I'm working on. Yes, I have a therapist.)
posted by Salamander to Human Relations (26 answers total) 4 users marked this as a favorite
he also thinks I am looking for hot rich guys, I'm only doing online dating for a bit of a laugh, and that I am only into short-term relationships

It depends a LOT on what you said that lead him to believe that, but man... that is kind of jerkish stuff to say if you ask me. Even if he did really believe that I think it is kind of rude saying that to you. Are you sure you want to ask him out again?

*IF* something you said/did justifies why he said that to you (which, again, I doubt), and you do really want to ask him out again, I would address that issue. Tell him that you aren't that way at all (assuming you aren't), maybe explain how you know it may have come off that way but that wasn't your intention. Then you can tell him that you really enjoyed yourself and felt a spark (or whatever) and then ask him out again.
posted by PuppetMcSockerson at 7:14 AM on March 21, 2013 [9 favorites]

Hey [Esteban]--it's been totally fun getting to know you! I think you're great, and I'd love to ask you out again--maybe next Thursday for dinner? I think I might have given you the wrong impression last time, and I'd love another chance, if you're willing. If not, it's my loss!
posted by Admiral Haddock at 7:19 AM on March 21, 2013 [2 favorites]

1) STOP BEING JOKEY. It gets in the way of being genuine.

2) BE GENUINE. Be honest with him. Tell him about your unease with meeting new people. It's not uncommon and it's understandable.


I'd write something like this.

"Dear First Name,

I really enjoyed the time we went out. I must admit, though, that I was super nervous. And that night I had a bit too much to drink and I said some things that I fear left you with the wrong impression.

I'm not someone who is just looking for short-term flings. With the right person, I can see something going long-term. I'm also not someone who is just looking for a rich guy. That's something I said as a joke and I'm sorry it came across seriously.

I'd love a second chance at making a first impression if that's possible. I swear I won't be drinking and I'll try my best to avoid silly little jokes that undermine who I really am. You had a good time with that person. I'd love for you to meet the real me.

So, how's about Saturday night at 8?


Good luck. :)
posted by inturnaround at 7:20 AM on March 21, 2013 [17 favorites]

It depends a LOT on what you said that lead him to believe that, but man... that is kind of jerkish stuff to say if you ask me. Even if he did really believe that I think it is kind of rude saying that to you. Are you sure you want to ask him out again?

Ahhh...I get that it sounds that way, but believe me...I think I was the only jerk in the situation.

I don't think it's one particular thing that I said, but more the way I answered his questions, and where the conversation went. It's honestly hard to say, because memories only came back to me in dribs and drabs over the next few days (I know, I know.) He asked me something along the lines of 'So, why is someone as attractive and smart as you doing online dating?' (which is a bit dumb in itself, I know), and my little internal hackles went up, and I answered something to the effect of, eh, just for a bit of fun. (I KNOW, we were both kind of tongue-in-cheek, but I'm cringeing just writing this.) But then he asked me about my past relationships, and I was flippant about that too. I was just so damned nervous, but my go-to response when I'm nervous is to act uber-confident and laugh everything off.
posted by Salamander at 7:28 AM on March 21, 2013

The fact that he's staying in contact means he's interested. Usually if guys aren't interested they don't contact you further, except maybe to explain they aren't interested.

So yeah, send him a brief explanation: clarify your values, explain that you were nervous and flippant, and suggest another meeting. Perhaps an activity with less alcohol involved this time :)
posted by bunderful at 7:35 AM on March 21, 2013 [1 favorite]

Hmm, I don't see anything super wrong about the example you gave - I think his question was kind of lame/condescending, or at least could have been worded a whole lot less jokily if he didn't want a jokey answer. But even if you absolutely DID come across as objectively gold-diggy, the problem here is that you are kind of in a 'down' position right now, where you might feel compelled to prove yourself to this guy - that doesn't sound like the right way to start a relationship.

So like PuppetMcSockerson, I'd at least think about whether or not it would be good for you to ask this guy out again - even if his impression was valid based on what you were saying, it COULD be a bad formula for a beginning relationship, depending on how the both of you handle it (and if it was valid, maybe take some time to work on whatever it is that's making you say these things). I'm not saying run for the hills necessarily, just ... be wary of letting this person define your interactions after the fact. Maybe it's all one big misunderstanding, but be aware of a possible dynamic where you are set up to have to apologize/be in the wrong.

With that said, if you do want to give it one more try, I think it will be important to not make a big deal out of the rich guys/short term relationship thing. "Hey [Name], I really enjoyed your email and had a great time with you the other night. I'm sorry if you got the wrong impression, but I'm definitely looking for [long-term relationships, or whatever you're looking for]. I'd love to get together again sometime if you're up for it - how about Thursday night at 7?" If you do go out again, try not to drink so much so you can keep a closer eye on what you said and don't have to rely on another person telling you afterwards what you were like. Watch out for overly jokey/defensive answers, but also try not to fixate on "making it up to him." Be yourself and see where things go. Good luck!
posted by DingoMutt at 7:42 AM on March 21, 2013 [4 favorites]

Ask him for a second First Date.
posted by Capt. Renault at 8:00 AM on March 21, 2013 [6 favorites]

Be careful about feeling like this is all your fault. To me, it doesn't sound like you did anything wrong, but that he's managed to turn this all around on you so you feel bad and grovel for his approval. Vulnerability isn't something you just hand someone on a platter - they have to earn it. It sounds like this guy is trying to force it out of you.

So he asked you some awkward questions that you answered awkwardly. That's it. If you want to see him again, yes, put the jokey stuff away and try being earnest for a little while. Say what you mean and mean what you say. But try not to be so quick to put him on a pedestal when you don't really know him yet.
posted by wondermouse at 8:01 AM on March 21, 2013 [20 favorites]

It doesn't sound like he's staying in contact to friend-zone you. It sounds more like he's a little insecure and challenging you to defeat his negative interpretations and assumptions. If that's right, it's not ideal, but greater clarity and additional reassurance may be all that's required to get this going.
posted by Monsieur Caution at 8:03 AM on March 21, 2013

Ask him out, say that in your drunken silliness you might have given him the wrong impression, but you'd really like to get to know him better.

As for being vulnerable, that's easy:

1) In your explanation about the silly stuff you said, own up to the fact it's a bit of a defense mechanism.
2) putting yourself out there again, saying "I'd like to get to know you better" is making yourself vulnerable, in a good way.

Like bunderful said, if he's still talking to you, he's interested. And his comment about what type of men he thought you were into shows he's willing to be honest with you.

An important disclaimer about learning to let yourself be vulnerable: remind yourself that if it doesn't work out, or he doesn't take you up on your request, it doesn't mean there is something wrong with you, it just means the two of you weren't the right fit. Fit is what matters.
posted by dry white toast at 8:03 AM on March 21, 2013 [1 favorite]

He's interested. Ask him out, and try to stay honest and open during the date.
posted by ead at 8:17 AM on March 21, 2013

I sit near the coffee bar at work, so i hear a lot of the office online dating stories.

Twelve years of casual conversations about this topic and I have compiled my research:

People over analyze shit.
posted by bobdow at 8:33 AM on March 21, 2013 [19 favorites]

I agree with Capt. Renault - word it as a request for a second first date, after an apology along the lines of "A ridiculous defense mechanism got in the way of me being as genuine and open as you deserved, and I want to apologise for that." Then tell him all the good stuff you wrote about him here and that you'd really like to see him again.

Like you said - nothing to lose, everything to gain. Nothing creepy about that.
posted by batmonkey at 8:42 AM on March 21, 2013

You've got nothing to lose by asking. The worst that can happen is that he says no.

If drinking too much on first dates is an issue for you, suggest meeting somewhere that doesn't serve alcohol so that you don't have the option of making the same mistake this time.
posted by asnider at 9:00 AM on March 21, 2013

Another thought: if BOTH of you got really drunk, as you said, then odds are good that neither of your memories about the night are spot-on accurate. His take on your behavior is probably just as colored by his pickled memory as yours, and may reflect his own issues or defense mechanisms. Again, I'm not saying that you should absolutely not give this another go or that this is a huge red flag or anything - it's just that you read as being a little too hard on yourself, so I hope you'll be wary of seeing things in terms of you needing to feel super-embarrassed and apologetic and him being in the right.

Again, good luck! I hope it does all work out and that the two of you can look back on this question together someday and chuckle about what doofuses you both were on that first date.
posted by DingoMutt at 9:16 AM on March 21, 2013 [1 favorite]

If I were you, I wouldn't engage with him at all about this. If you want to ask for a second date, do so.

However, I feel funny about the idea of someone telling you about yourself and then you having to prove that you're not like whatever negative thing they told you about yourself. Maybe it is a straight-up misunderstanding, but this is also a classic pattern that manipulative people use. I also think that this doesn't combine too well with him supposedly wanting to see you but being just out of reach. That also strikes me as manipulative. Not that I'm suggesting this guy is Beelzebub, Prince of Lies or anything; only that a lot of people are quite manipulative, just in general, and it's worth making a note of this sort of thing when it comes up.

So if you take this further, I wouldn't give him any more acknowledgement of what he said about you. I'd just suggest an occasion for a second date. Perhaps something incompatible with drinking so that you can get a clear picture of each other's true attitudes.

Also, this is one definition of a "neg" - tell the HB something slightly insulting about herself and then leave it to her to "qualify" herself to you - but it's insulting enough that I think it counts as a misuse of the concept of a neg. A neg played fairly would be something like giving a compliment and then adding a jokey backhanded punchline, so that a compliment is still conveyed but is then pulled back from the brink of being smarmy. If this guy was trying to neg you, I don't particularly like the way he did it.
posted by tel3path at 9:34 AM on March 21, 2013 [7 favorites]

Interesting - telepath, could you please clarify which comment of his you were referring to in your last paragraph? I'm familiar with the general concept of 'negging', just not sure what the neg was here (or what 'HB' means). Thanks! :)
posted by Salamander at 9:42 AM on March 21, 2013

"So, why is someone as attractive and smart as you doing online dating?"

What a dumb question. Are only stupid and ugly people supposed to use online dating? Does he not consider himself attractive or smart since HE'S using online dating? Is he under the impression that attractive, smart women have relationship partners show up on their doorstep?

To me it's a bit of a red flag that he was kind of asking you these questions that put you in a position where you felt the need to defend yourself... it makes me worry that he was trying to "neg" you as tel3path suggested.

I'm not saying don't go out with him. Since you're already messaging back and forth, I think you should definitely cut to the chase and say something like, "Hey when are getting drinks again?" But then on that 2nd date, proceed with skepticism.
posted by Asparagus at 9:51 AM on March 21, 2013 [1 favorite]

The "neg" I was referring to is where he told you you came across as a gold-digger who isn't after a long-term relationship.

It looks, to me, like this is intended to get you to beg him to be in a LTR with you while going out of your way to never cost him any money, ever.

Or maybe he really thought so, but, if he has so low an opinion of you and is willing to express it, I'd wonder why he was still in contact with you? Odd.

The whole "why is someone as attractive and smart as you doing online dating" is a lot closer to the neg as it's supposed to be. It would seem to invite a playful response such as "why, for the same reason you are, Handsome!!! [giggle!]"

Anyway, though I don't like what he said about you being a golddigger and etc., and I also think it's important to pay attention to small warnings - it may also not be that serious. What I do think you should remember, though, is that you're not the only one who has something to lose by making a bad impression here. You can't focus only on what you might have done to screw this up since he clearly isn't beyond criticism either.
posted by tel3path at 10:16 AM on March 21, 2013 [3 favorites]

Overthinking. He is interested. Go out again.
posted by TonyRobots at 10:34 AM on March 21, 2013

Sorry, I'll go away after this, to avoid thread sitting, but I need to clarify: he never used the term 'gold-digger', or I would totally have thought he was a jerk. I don't think he thinks I'm looking for a rich dude to sponge off, more that I come from a slightly different socioeconomic background than him and he assumes (incorrectly) that I'm looking to 'date up', or something. I also don't think he's a cheapskate, but he is divorced with kids, and maybe a bit insecure about that. Anyway, all the insights are very helpful, so thank you.
posted by Salamander at 10:35 AM on March 21, 2013

I think folks are being a little hard on your date. That thing about why you're doing online dating? It was intended as a compliment! A little Woody Allen-esque "what's a beautiful woman like you doing dating a guy like me?" I don't think he expected a thousand internet strangers to be dissecting it.

Definitely ask him on a second date and don't be overly apologetic about it. If you're looking for a long term relationship, you can tell him so, it's not 'too serious' - most people have that information right up front on their online profile.
posted by treehorn+bunny at 10:37 AM on March 21, 2013 [2 favorites]

I dunno.. I haven't done online dating myself, mainly to avoid the interviewing that seems to go along with a formal first date. It sounds to me like he went in with an idea of the kinds of responses he was after (like most people, probably), and was probably just guarding himself, for the reasons you've mentioned (though, are you sure about the SE stuff, on his side, or is that coming more from you? Do you feel a need to impress him, that way?).

I agree with keeping apology to a minimum - ask him out, maybe mention nerves if you want but no more explaining than that. If it's a go, maybe choose an activity, vs. a sit-down dinner, to shake off some of the seriousness from which it seems both of you are suffering.
posted by nelljie at 10:54 AM on March 21, 2013

"So, I've been thinking about how much I enjoyed our date, and it seems a shame to stop there. Any interest in a second date, or should I move on?"
posted by davejay at 11:31 AM on March 21, 2013 [3 favorites]

Thanks so much, everyone - all the answers really helped me to process this more objectively.

I am going to message him tonight with a combination of brief explanation + invitation for another date, and let the chips fall where they may.
posted by Salamander at 9:36 PM on March 21, 2013 [1 favorite]

Final follow-up: so, I did it. I sent the message, and he sent a really nice reply. The gist of which was, he's met someone he really likes and has already been on a few dates with her, so is putting all other activity on hold until he sees how it works out.

I replied and thanked him for his honesty, and closed the match.

Not the outcome I was hoping for (obviously), but I'm still glad I tried. Thanks for all the advice.
posted by Salamander at 12:28 AM on March 28, 2013 [1 favorite]

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