Am I going about online dating correctly?

October 8, 2012 7:02 PM

This online dating thing is sort of working out, in that I'm getting dates with great people, but it never seems to move beyond 3-4 dates and I'm getting the kind of vagueness I got when I was in high school. How aggressive do I need to be?

I'm a late 20s male...

I got sort of tired of hookups at the bar scene, and got into online dating a couple months ago. I've learned to filter the social outcasts, and non-normal people (while non-normal is great I don't need people with a lot of problems). I've gone on a lot of dates but here's how it seems to go:

- I get a lot of positive feedback, and get sort of dragged on a lot of dates where there's not a lot of sexual intimacy but things go good. I sort of reach a point where I'm tired of taking it slow (I'm talking 10-11 dates) and push the issue, and get a, "Just not into you but let's be best friends!" sort of thing. Sort of gotten better at weeding this out.

- I always find myself always initiating dates, which makes me a bit apprehensive, but I get a lot of text/online feedback after the first couple of dates. The dates go great, and I get a lot of conversation but hit a wall when trying to plan date 4+.

So basically I get a lot of dates, really great dates, but get a lot of vagueness and a "I'm busy this week," type of thing. I've been a lot more clear in whether or not I'm interested in being more than just friends, "I really enjoying hang out with you!" and then vagueness or, "Yeah I had a great time!" but when I ask when we will hang out again it gets evasive.

I'm used to having a great date on Friday/Saturday, getting good or negative feedback, and then immediately trying to figure out when we'll get together. Without fail, with online dating, everyone seems really busy and too cool for school, followed by perhaps an intense date, and I always feel like the pursuer. It really feels like when I was in high school or college and the people I dated didn't know what they wanted.

Is this normal? Anyway to get around this? Part of me is being practical, dating is expensive and if by the 2-3 date you're not interested in being more than friends, I want to suss this out. Would it be wrong to cut things off by the 2-3 date without blatant sexual contact (beyond making out)? I guess what it boils down to is that I have a very active, vibrant social life. I have a lot of friends, I don't want to make more friends of the opposite sex, I want to date someone. I don't want to spend two months trying to figure out if the person has any interest or not.

Is this how things normally work out, should I be more aggressive and if so how? Or will being more aggressive turn people off?

And to tell you that I'm thinking too hard on this, when I've had usual one night stands or dates with people in real life, which I've been on a lot, I can tell really quickly whether or not they are interested. Online dating has baffled me, but I've only been on 12-13 online dates? Perhaps too small a number?

Sorry if this sounds rambling, but I feel as if I regressed 10 years overnight, this might just be the nature of dating strangers on the Internet. Starting to get frustrated with online dating, and I'm trying to figure out if it is me or if I'm approaching it wrong.

posted by anonymous to human relations (24 answers total)

As far as I'm concerned, the huge systemic problem with online dating is the same as its strength - an enormous and constantly-replenished pool of people to choose from. Far more than in real life, there's a sense of limitless possibility: there are always more profiles to look at, always different searches you can type in, always more inbox messages to weed through. I speak as a woman who did online dating. My hunch would be that the people you're dating are also concurrently juggling lots of other people, and are juggling all of that with the potential of even more people whom they have yet to meet, with no real deadline or anything else fixed to structure decisions and firm commitments around. They're not only weighing you against other dates they're currently having, but also against dates they might have in the future based on messages in their inbox, and against even more distant dates they might have even later with hypothetical people on the site. This is particularly true if you live in a major metropolis (NYC, Boston, LA, etc.), and don't have huge deal-breakers that rule out large swathes of the population (no premarital sex, must be Buddhist, or what have you).

Perhaps others can offer more concrete suggestions, but my sense is that this is a fundamental problem with the medium itself (while recognizing its positive potential in bringing together people with fringe values or interests who wouldn't otherwise have met, etc.)
posted by UniversityNomad at 7:16 PM on October 8, 2012 [11 favorites]

Dear OP - Do you mind adding a location?
posted by msamye at 7:19 PM on October 8, 2012 [1 favorite]

dating is expensive ...Would it be wrong to cut things off by the 2-3 date without blatant sexual contact (beyond making out)?

It doesn't have to be expensive - many dates can be free, and many others are no more expensive than a night out with friends. You don't have to be going out for expensive dinners or anything like that.

Cutting things off after 2-3 dates without sex seems really extreme. I guess if you're looking for casual sex/FWB it might be a good strategy, but I see it backfiring hardcore if you're looking for a relationship, since MANY women looking for a relationship will either not be comfortable with sex that soon or will purposefully avoid sex for the first few dates.

Online dating does seem to be more flaky than other mediums. Still, many people find success. It's frustrating to see things stall out but it's very much par for the course - many people struggle to get first dates with someone interesting from online, let alone multiple dates. It is in large part a numbers game, even more so than meeting people in real life.
posted by randomnity at 7:27 PM on October 8, 2012 [7 favorites]

Women are socialized to never explicitly say "no," especially to men. Therefore, "maybe," "I'm busy this week," and general vagueness usually mean no.

You're putting in the perfectly appropriate amount of effort. If someone isn't reciprocating that effort, she's not into you, move on.
posted by telegraph at 7:33 PM on October 8, 2012 [2 favorites]

Your experience has been my experience too. I chalk it up to the awkwardness of the online dating "format," because the first time you're seeing and speaking to the other person, you're trying to figure out if you're attracted to them. Some people know right away, but I don't, and I'm betting a lot of others don't too. When you're dating someone you've met in real life, you know you're not unattracted to them and -- as UniversityNomad said -- you aren't thinking about them in terms of how they fit into all of your other options.

So I think it would do you well to tell the women you meet that you're looking for a girlfriend. I would be glad to know up front what your interest is, both in general and in me, because it saves me time from guessing. This kind of honesty doesn't have to be aggressive. Just say it straightforwardly. Other girls who have fallen into awkward friendships or unspoken casual relationships from online dating would appreciate your honesty, and if they can't tell you honestly that they're not interested and give you "I'm busy"s, move on.
posted by houndsoflove at 7:36 PM on October 8, 2012 [1 favorite]

I think 3-4 dates is way too quick to cut someone off for not sleeping with you. That being said I would think it a bit bizarre if the subject of sex hadn't come up by date 10-12. Honestly, if things haven't fallen into a natural rhythm by that point that more resembles a relationship, if an undefined one, as opposed to dating I think you have your answer.

I think you handle this by gently pressing the issue and by that I don't mean pressuring her into sex. I mean invite her over to your place for dinner and a movie after maybe after date 3-5. If she doesn't seem excited by the idea or suggests something else or goes running out of your apartment at 8:30 you know she probably isn't feeling it. That being said if she straight up tells you she likes to go slow with the physical side of things I would stick around because a person doesn't put themselves out there like that if they don't like the other person. Which is to say willingness to jump into bed with someone is not always an indicator of their interest. But yeah if by date 4 or 5 you're still having polite conversation over dinner and a chaste hug goodbye at the end of the night I think it's fairly safe to say there is clearly not enough chemistry and/or interests on both ends to pursue it further.

Also, I have to wonder why you are dating so many women for so long with not much positive feedback. Do you even like them? I may be totally off base, but maybe your problem is you're dating women who objectively meet your criteria, but you don't really have any connection with. You're going to meet lots of women who on paper seem like good matches, but in reality you in no way click with. Online dating really can put in that headspace of essentially comparison shopping for dates when that is the last thing you want to do when trying to forge a relationship. So yeah maybe you need to be ending things with these women far quicker, not because they won't sleep with you, but because they clearly aren't the one for you and you aren't the one for them, and their actions convey they are only half heatedly into it.
posted by whoaali at 7:44 PM on October 8, 2012 [3 favorites]

As a woman, the thought that a guy is mentally adding up the amount he's spent before I put out is a bit... icky. And though it sounds new-age, a lot of women pick up on 'vibes' you're sending out even if you're not actually saying anything. Some men I've known have found this hard to understand. So your question 'do I need to be more aggressive' - you need to relax, enjoy someone's company, get to know them and have no expectations from there.
posted by pink_gorilla at 7:52 PM on October 8, 2012 [21 favorites]

I always find myself always initiating dates, which makes me a bit apprehensive

I always feel like the pursuer

For what it's worth, women are heavily socialized to let the man be the initiator (I'm being heterocentrist and assuming you're male). So I wouldn't frame this in terms of, "what am I doing wrong" or taking it as a negative reflection of your own attractiveness. Likewise,

there's not a lot of sexual intimacy but things go good

Are you trying at all to initiate physical/sexual intimacy/flirting before date 10 or 11?
posted by availablelight at 8:38 PM on October 8, 2012

Also, one more thing, to build on what whoaali said. In your post, there's a lot about your frustrations about and expectations of the women you're dating, but very little about you. Rather than concentrating on external signs of perceived validation from these women (accepting more dates, having sex with you, etc.), it might be helpful mentally to reframe.

It sounds like you ultimately want a girlfriend, and a monogamous relationship, and to stop dating multiple people. From your post, it sounds almost as though any woman who would date you and sleep with you for 10 dates you would ask to be your girlfriend. I really doubt this is the case. What would make you choose one of these women over all the others? You're not comparison shopping for toasters, here, assessing qualities on paper; rather, you're trying to find someone who not only is attractive to you and has qualities important to you, but with whom you click, and with whom you intuitively have a sense of kinship (presumably). It might be worth thinking about a timeline for this. How many dates do you think you could reasonably determine this in? Do you need to have sex with a woman to determine this? What do you think might make you feel reasonably sure that one of the women you're dating is a women with whom you want to have a relationship? If it's important to you that you share certain interests, hobbies, or values, you might think about restructuring your dates to suss these out more accurately and more quickly, which might help her do so as well. For instance, if your passion is for classical music, you might go to the symphony together, or get cheap tickets to a university performance of something; if you are religious, you might want to attend a service together, which would naturally lead afterwards into a discussion of religion and values; if you are interested in social justice, you could have a date where you volunteer at a soup kitchen together, which would be a prime time to discuss social values, etc.

I have often found personally that generic dates are a poor way to assess whether or not I'd be interested in a relationship with someone: at best, you get some good conversation, which can be an indication, but the environment is often artificial and stilted, and you don't get to see them interact with any others besides yourself. Also, you don't get to see them animated by their passions, which is often for me the most indicative of how endearing I find someone, and whether I could see myself wanting to share in that. What I'm saying is that instead of worrying about progressing to the next sexual or face-time level with women, generically, it would be worth thinking about what exactly you're looking for, and exactly how you might more easily and quickly determine whether a given woman might fit that. Creating specific dates and shared experiences centered around whatever it is would probably help both of you make decisions more quickly, because you'll be engaging with things that are deeply meaningful to at least one of you. I have also found that engaging with things that I'm passionate about with someone else who is passionate about them can help create a spark between us, far more than a movie and some nondescript conversation. Doing something together is also far less inhibiting, and you feel less like you're watching a rehearsed monologue or are at a job interview: when you get to see someone acting naturally, you get a much clearer sense of how they are as a person.
posted by UniversityNomad at 8:44 PM on October 8, 2012 [6 favorites]

You're doing okay, as things stand. It is normal to want a longer-term relationship than a fling, so I wouldn't sweat it too much. Savour the moment, is how I'd put it.
posted by the cydonian at 9:18 PM on October 8, 2012

So, I met my SO through an online dating site. I wasn't on the site long, but based on my experience as a woman roughly your age, my gut response is that you're not reading these women's signals correctly. That is, what you're interpreting as mixed signals are, in fact, gentle blow-offs. Once you get better at spotting a non-starter, you can cut your losses more quickly and move on.

I always find myself always initiating dates, which makes me a bit apprehensive

I think this is absolutely right on your part -- NOT because you *should* be the pursuer, but because it's just the safest route for you to take. Women are socialized (and often, explicitly instructed -- by books, friends, etc.) not to initiate plans OR communication before they are in a clearly defined "relationship" with the object of their affection. Absurd, yes. Frustratingly retro, yes. But even progressive, feminist women can fall prey to this message, so if you don't want to miss out on the lady of your dreams, keep initiating the dates until she feels comfortable enough to take the reins.

I get a lot of conversation but hit a wall when trying to plan date 4+.

When I was doing the online thing, I always accepted a second date, no matter my feelings about the first date, unless the guy seemed like a creep. I mean, we all get nervous, and first impressions can go awry. The second date actually felt more like a traditional "first date" (the first date in this instance being a screening process to determine that the guy was sane and honest in his self-representation online).

If the guy seemed like nice company on the second date, I'd accept a third, to see if there was real chemistry once all the nerves began to subside and we had a chance to move beyond the "getting to know you" small talk. But if there was no spark on the third date, that was when I cut bait.

All this to say, it makes perfect sense to me that you hit a wall when trying to plan date 4. If the woman does not respond eagerly to your invitation to a fourth date, cut bait immediately and go fish elsewhere. (Conversely, if she's feeling it after the third date and she's not into games -- you don't want someone who's into games, do you? -- she will accept your invitation eagerly and quickly, OR, if really busy, suggest a concrete date in the future.)

Without fail, with online dating, everyone seems really busy and too cool for school

If you try to set up a date and she doesn't find a way to accept the proposition, cross her off your list and move on. Our irksome gender norms cast you in the role of pursuer, but I know of no social pressure that inhibits a woman from trying to find a way to hang out with the new guy she's super excited about.

Would it be wrong to cut things off by the 2-3 date without blatant sexual contact (beyond making out)?

You're going to be excluding a lot of awesome women if you adopt this rule. I'm not a fan of moving beyond some heavy making out unless I know I'm with someone I want to keep seeing for a while, and judging by my friends, I'm far from alone in this.

I think you can tell with some heavy necking if you and the lady feel the chemistry or not. If you're interested in judging whether she wants a relationship, far better to judge by how swiftly and positively she reacts to your proposals to meet up again.

I don't want to spend two months trying to figure out if the person has any interest or not.

I understand this. Two months is far too long to gauge whether someone has any interest. It's about the right amount of time to decide if that interest is going to lead into something more exclusive, though.

Hope my perspective here was helpful, although I am fully aware that my answers will be very different from someone else's, as we're all individuals and whatnot.
posted by artemisia at 9:19 PM on October 8, 2012 [10 favorites]

One thing you might consider is simply this: go on two dates, since two dates seems reasonable for you to achieve often. Then, when planning the third date, don't say "when are we going to go out", but instead say "I've really enjoyed the two dates we've had so far, and I'd like to take you out again. Before we make plans, though, I'd like to be up front with you: I'm interested in taking this further as a potential future relationship, not a friendship. Do you feel the same way, or should we both move on?"

I mean, nothing wrong with being up-front and honest, right?
posted by davejay at 10:10 PM on October 8, 2012 [3 favorites]

Would it be wrong to cut things off by the 2-3 date without blatant sexual contact (beyond making out)?

Wrong or not is really up to you. Are you looking to have a relationship that leads to blatant sexual contact by the 2nd or 3rd date? If so, then cutting it off if it doesn't happen is the right thing to do. Are you looking to have a relationship with a person that includes sexuality? Then you should probably have a good sense as to whether you're attracted to her by the end of the 2nd date, even without kissing, and there's nothing wrong with asking whether she's considering you as a friend or as a potential romantic partner. It is more romantic not to have to ask, but if you feel like you don't know, you can either write it off and move on, or ask because you have nothing to lose.
posted by davejay at 10:13 PM on October 8, 2012

Yes, you have to be more aggressive/outgoing or be OK with it taking longer to find the person who is on your wavelength. The former is building a bridge to someone, the latter, walking a path until another path crosses yours. You can also mix and match, because depending on who you are, dating someone for a month or three might be better than going on the same 4 dates with different women over and over. People say online dating is a numbers game, and it can be, but there's a counterpoint of possibly being a waiting game.
posted by rhizome at 10:17 PM on October 8, 2012

There's no wall here. Four dates is how long it takes to decide you're not quite connecting with someone, when there's no otherwise obvious turn-off.

Just keep looking and focus on the specific kind of person and form of connection you desire. Not just a warm body.
posted by ead at 10:47 PM on October 8, 2012 [1 favorite]

So basically I get a lot of dates, really great dates, but get a lot of vagueness and a "I'm busy this week," type of thing. I've been a lot more clear in whether or not I'm interested in being more than just friends, "I really enjoying hang out with you!" and then vagueness or, "Yeah I had a great time!" but when I ask when we will hang out again it gets evasive.

Yes, this is a woman politely blowing you off. It may seem frustrating, but history has taught us that if a guy asks us out and we say something like, "No, thank you," we're likely to get a message back calling us a bitch or worse. A lot of guys get aggressive if you reject them directly. The gentle fade-out is much easier.

Would it be wrong to cut things off by the 2-3 date without blatant sexual contact (beyond making out)?

You can choose to cut things off whenever you like, but you're probably going to miss out on some great girls this way. It takes a lot of women -- and, I would say, quite a few men -- more than three dates to decide if they like somebody like that, and even if they do, they may not be ready to jump into bed with them.

I think maybe you need to work out what you really want here. There's nothing in your post about wanting to meet a woman who is, say, kind and intelligent and has a great sense of humour. There's a lot about meeting a woman who'll have sex with you and by which date she'll do it. It makes me think you're looking less for a girlfriend and more for a regular fuck-buddy kind of thing. Which is fine, but by being honest and upfront about what you want, you may save yourself a lot of frustration.

Otherwise, if you decide you really do want a girlfriend, a more relaxed approach may prove beneficial. Work on finding somebody you connect with mentally and emotionally, and the physical stuff will most likely take care of itself.
posted by Georgina at 11:49 PM on October 8, 2012 [1 favorite]

I think there's a middle ground here. Cutting off anyone who doesn't get in bed with you by the 4th date is not a good strategy, as people have noted you're going to narrow your dating pool considerably and miss some really great women. However, cutting off anyone who isn't excited to spend time with you by the 5th-6th date is a reasonable rule that doesn't reject women unnecessarily but lets you move on to someone who is more interested.

As people have said, with online dating you're starting from scratch, or less-than-scratch. So the first date or two are usually pretty timid, and that's good if you ask me. But by the 3rd date they should have a good sense of whether they like you, and by the 5th or 6th date if they're still wishy-washy then let's be honest: they're not that interested and they're just being hopeful at that point. Do yourself and them a favor and move on if by date 5 or 6 they aren't excited to take your calls, aren't making time to see you, or don't seem to be very passionate about you (not necessarily sexual, but emotionally excited and letting you get a bit closer).

How to suss out who's blowing you off? Fairly easy. "I'm busy this weekend - could we find a time next week or the week after?" That's them being honest and trying to make it work. You counter-offer with a date idea that fits her schedule and yours, and if she takes it then she's interested. So the "I'm busy" plus a suggestion of when would be a better time is an honest "I"m busy," and the suggestion of another time indicates interest. Run with these, there's potential there.

"Sorry, I'm busy." No suggestion of when you could get together is a bad sign. When someone says they can't hang out, and does not suggest another time, that's the signal that you're getting blown off. Just in case, you can reach out to them once or twice more, because maybe she just didn't think of a good time to meet. Maybe go on another date. But honestly, if they're wishy-washy before date 4, and they're wishy-washy before date 5, back off. Maybe she's a bad communicator, but life's too short for you to spend too much time figuring out whether she's uninterested or just a poor communicator. Neither is a very good thing, and honestly it's probably the lack of interest.

Finally, there's a big leap from making out to full sexual contact, and I think you need to recognize that. There are little pecks, limp-fish making out, then there's passionate making out. Really, there's no need to have sex in order to determine a woman's level of sexual interest in you. She'll make out with the same level of interest, even if she's not ready to go further. After the second or third date, go in for a kiss. Does she reciprocate? A time or two after that, find some time alone and make out a bit. If she doesn't want to, or if she's limp and there's no passion, then she's not interested and you can move on. Someone who is interested will give you a get into it, even if "it" remains a PG-13 make out season for now.
posted by PCup at 4:49 AM on October 9, 2012 [3 favorites]

The vague answers you're getting from the people you're dating are actually brush-offs and they think they're being kind or polite about it.

Online dating is a numbers game. You will have a whole lot of interactions that fizzle and go nowhere and a small few which are exciting and awesome. When those happen, the other party will be equally excited to see you or talk to you or whatever.

Other than keeping track of how much you're spending on someone or setting a hard limit on how soon they need to put out, you're not doing anything wrong - you just need to relax and keep at it.
posted by FAMOUS MONSTER at 5:44 AM on October 9, 2012 [1 favorite]

Agree with everyone above who says that non-committal responses are almost always no in disguise. There are some people who are just flakey. But even if they were interested, I wouldn't want to be in a relationship with somebody where I really have to work to nail them down on anything and it sounds like you don't either.

Artemisia and PCup have good advice. I would add a few things:

- You're right, online dating can be expensive and time-consuming. Maybe you could standardize your meeting process to improve that. It doesn't sound like this is a problem for you, but don't spend too much time emailing back and forth. I learned that this was sometimes a big clue to a relationship being a non-starter. By about the second or third email exchange, I usually suggested meeting if things were going well. (I'm a woman, btw, but probably more aggressive than a lot of other women about being the one to suggest meeting.)

- After a while, I learned that it was better for the first date to be in a coffee shop or maybe at a bar during the day. Just grabbing a drink with someone, seeing each other in person, some light conversation, and you're not tied there for more than 30-45 minutes if things aren't going well AND it's very inexpensive. I think it also sets you up well for the second date, which can be more like a traditional first date.

- I don't know if maybe this is an issue, but are you communicating with your dates in a way that's very casual? Personally, I don't like being asked out via text message, Facebook, or IM. Email is ok, phone is the best once a person has my number. I just feel like the other mediums aren't very personal and don't take much effort. Not that they need to rent a skywriting plane to ask me out for coffee, but I guess I like to feel like I'm not part of a form letter campaign to get laid.

I fully recognize that my preferences are probably unusual for someone my age (I'm in my late 20s). But if you're asking people out over text message, a lot of people see this as a very casual form of communication that doesn't always need to be responded to right away. Even if they're fine being asked out in that way, it may not have the sit-up-and-take-notice impact that a phone call or email would. If you make that little bit of extra effort to call people you're really interested in to ask them out, I think it will make you stand out and it may also help you read people better to see if they're interested. I think you can tell a lot more about a person's feelings towards you on a phone call then on a text.

- I think my biggest lesson from online dating was BE STRAIGHTFORWARD. If you like someone, tell them. If you want to go on another date, tell them. If you're confused by the way they're acting, tell them. There is nothing wrong with saying, "I really like you and want to keep seeing you, but I'm getting the feeling that you may not feel the same way. Is that the case?" I know that anyone who can't handle or doesn't want that kind of clarity in their relationship is not for me. Do not be afraid to express what you want or ask for clarification.

I think there's a misconception that this kind of directness ruins the romance. Sure, if you go around talking about your feelings like a robot and never actually demonstrating them, it will not feel very romantic. But what REALLY kills the romance for me is uncertainty and anxiety. A lot of the pick-up artist stuff is based on making people feel insecure and unstable. This may get you laid, but it's generally not a good foundation for a healthy relationship.

- Being straightforward is also somewhat a good idea on the sex issue. I agree with everyone above who pointed out that you're going to be excluding a lot of great girls if you set a hard three date sex limit. If you're into someone and you think they're into you, tell them you find them attractive. Be physically affectionate (arm around the waist, small touches here and there). The response to those things will tell you whether or not there's potential for a sexual relationship. Being straightforward doesn't mean blurting out, "I want to bone" at the conclusion of Date 3. It just means being transparent with your attraction, both verbally and non-verbally.
posted by Colonel_Chappy at 8:13 AM on October 9, 2012 [5 favorites]

10-11 dates is a lot of dates with one person if the two of you aren't interested. Is there sexual chemistry on these dates? I don't mean sexual intercourse, just sexual interest.

In my experience it NEVER took more than three dates to figure out whether there was mutual interest. Someone might seem perfect "on paper" but by three dates I knew whether the other person was interesting and whether she was interested. I don't know if I would suggest any kind of cut off after just three dates...but if you are going out on ten dates and you are still even wondering if you are interested, time to move on.

You will have to go through A LOT of people, which is ok. Online is no different from any other medium in this regard.
posted by massysett at 9:04 AM on October 9, 2012

From the OP:

Thanks everyone for your responses. I guess the main problem I have with internet dating is that with non-internet dating, by the time you're going on dinners and drinks and doing very datey things, usually you've known the person and have sussed out whether or not there's chemistry there.

I guess I need to be a bit more casual about things and picking cheaper things to do or about splitting the check. I'm totally fine with meeting new and interesting people, but it is not feasible for me to drop several hundred dollars on dinner and drinks every time we go out. This is my problem though.

Also by "more aggressive" I didn't mean it in a sexual fashion, I meant as far as cutting people off, or at least eliminating them from the dating pool. Again, my previous experience, I could always rely on a group of friends or seeing someone in person to know kind of suss out how they feel, whether, "I'm busy" is really busy or not, text or chat is a weird medium for this sort of stuff. Usually I'm good on picking out this sort of thing.

"I really like you and want to keep seeing you, but I'm getting the feeling that you may not feel the same way. Is that the case?"

I think this is the best advice, not something I'm used to doing, especially early on (3-4 dates), but I think it would be best. I sort of feel like this feels desperate but if I was into someone and they sent me this, I would totally reply enthusiastically. Again, with non-internet dating, you can usually pick up on this more naturally, or at least I have.

Re: Wishy-washy issue, when I bring up the texts/conversations with friends, they go, "She's totally into you! Just seems busy," but I think they have no experience with Internet dating. I agree that it is being blown off, though I'm used to no response or a curt response, along the lines of, "I had a great time, but let's just be friends" speech. I don't seem to get that with online dating, which is weird, but now I know.

Oh and the sex thing, I think you guys made too big of a deal about that, though perhaps I made too big of a deal about it. I was sort of using it as a proxy for not being direct and straightforward.

Hope this helps anyone looking at this in the future!

posted by jessamyn at 9:39 AM on October 9, 2012

Several hundred per date!?!?!

Ok I have found the source of your problem. You are throwing an insane amount of money at these women extraordinarily early on the relationship. That is millionaire matchmaker money and I'm going to assume that isn't the arrangement you are going for. I'm not going to call these women gold diggers, but I will say its hard to turn down what sounds like a free five star dinner. I mean who wouldn't give it a few more dates to see if feelings develop if you're getting wines and dined like a Rockefeller.

Here's what you do:

1st date - drinks during the week or coffee on the weekend. Nice, but not crazy expensive bar. Your bill for the both of you shouldn't be more than $40-50 and that's at the very high end assuming you are in a major city. Otherwise you can probably almost half that.

2nd date, same as first or casual dinner. Somewhere casual, nothing crazy. Maybe $60-80 max. It's perfectly fine to go Dutch, but it's also fine to pay.

Date 2-5: repeat some version of above. Maybe throw in a movie or other moderately priced activity.

If you do this I bet you'll be getting some much clearer signals much more quickly.
posted by whoaali at 10:16 AM on October 9, 2012 [3 favorites]

Thanks everyone for your responses. I guess the main problem I have with internet dating is that with non-internet dating, by the time you're going on dinners and drinks and doing very datey things, usually you've known the person and have sussed out whether or not there's chemistry there.

When I was dating online, the norm was that Date 1 was really just getting coffee somewhere. The goal was not to impress (or be impressed) with a fancy expensive meal or a clever idea for an activity or whatever. It was just, like, (1) "I want to confirm that you are a real person who will actually show up," (2) "I want to make sure you're not horribly tedious or creepy in person," and (3) "I want to see if there's at least some slight chance of sexual chemistry." And then even Date 2 was more likely to be a cheap meal somewhere rather than the full dinner-and-a-movie-and-drinks ritual.

Similarly, people tended to signal Serious Interest (by e.g. kissing each other or taking their clothing off or discussing exclusivity or whatever metric you're using) a little later in the game.

Look at it this way. The first and maybe even second times you meet up IRL are not Real Dates. They're basically the equivalent of spending some time chatting at a party, trying to decide if it's even worth being all "what's your number?" If you agree to meet up a third time IRL, that's your First Real Date, the equivalent of "I got her phone number, I called her up a week later and we went out to dinner." So you do get a little extra time to check whether there's chemistry before you're in Full-On Real Date Mode together.
posted by nebulawindphone at 10:48 AM on October 9, 2012 [2 favorites]

I'm totally fine with meeting new and interesting people, but it is not feasible for me to drop several hundred dollars on dinner and drinks every time we go out. This is my problem though.

Several hundred dollars?! No. You're sending the wrong message with that alone. Keep it casual and low pressure in the beginning. You're just getting to know each other; there's no reason to be spending hundreds of dollars on each other yet. It makes you look either desperate or like you're trying to pressure her into sleeping with you early on. As a non-gold-digging woman, I can tell you that's how that would make me feel.

If you're looking for a girlfriend, an actual relationship and not just an easy hook-up, look more for stuff you believe in strongly upfront, rather than simply filtering out the ladies who strike you as freaks but otherwise being open to whatever. It just sounds like these ladies are kind of generic to you with how you worded your experiences. Think less about the quality of the date itself than about the quality of the individual person you're getting to know.
posted by wondermouse at 2:05 PM on October 9, 2012 [1 favorite]