How to date two women at once?

August 9, 2006 7:35 PM

How do I date more than one person at a time?

So, I'm doing the online dating thing. And what's normal and what's convenient seems to be talking with several people at once and setting up dates with more than one person in a given time period.

So, several women at a time? Lots of dates? Sounds good, right?

But I'm not sure my brain works that way. It just seems weird to go on a date with someone and know that I have another one scheduled the next day or week. And then even after a good first date, it seems to be expected that you doesn't necessarily stop setting up other first dates until you mutually decide to become exclusive.

So an easy solution is to just date one at a time, duh. But I was wondering if the MeFi studs and studettes had some advice for how to deal with the multi-dating situation.

For the record, I'm most interested in a monogamous relationship with potential for marriage sometime (probably a couple of years) down the line. One night stands aren't out of the question, but they're not a priority, either. And I certainly wouldn't mislead someone to have one.

posted by callmejay to Human Relations (23 answers total)

Best answer: If it's just dating and not a relationship then there is no moral quandary. Be honest with who your dating and mention that you're currently playing the field. A lot of women would appreciate the honesty (some definitely would not, but that's the way life works).

Best suggestion? If you want to avoid some of the possible faux-pas (using the wrong name, mixing up interests etc.) then keep a journal after each date and do your homework before heading out for the date. This really depends on your memory and the volume of women you're seeing, but it is foolproof.

Again, I can't stress the honesty aspect. Oh, and if and when you decide to stick with one girl burn the journal.
posted by purephase at 7:51 PM on August 9, 2006 [1 favorite]

I can't see there's any problem with that. I did a similar thing - just going out with a few different women here and there, no commitments at that time, and nobody was upset.

I wouldn't have been upset if one of them had told me they were doing the same, as we weren't in a relationship at the time anyway.
posted by tomble at 7:57 PM on August 9, 2006

Best answer: I actually think that with online dating, it's pretty safe to assume that the women you're going on dates with are also in the same situation. So if the monogamy thing is an issue, knowing that should help.

It's funny, my female friends who are also doing online dating and I always talk about how hard it is to date multiple people at the same time, whereas men tend to do it all the time (they "play the field"). So it's actually kind of refreshing to hear a guy asking this question :-)
posted by echo0720 at 8:07 PM on August 9, 2006

there are studs on mefi? I thought we were all nerds. ;)

I'm in a similar boat; i too am not entirely comfortable with playing the field anymore; would rather try them on one at a time. But I've learned to "speed up" the process a bit; hard experience has taught me what i like and dont like; what is sure to fail and what has a chance. I can tell within about 3 dates whether or not there are going to be any obvious long-term deal-breakers. If yes, "next". If no, I continue dating so long as it continues to go well.

The trouble with that is if you get deeply emotionally involved and THEN discover the deal-breaker. Then its a bummer for everyone. Hard to do the right thing once you're in it up to your neck. But I think there are things you can do to avoid that to some degree once you know yourself and what you like and dont like in a relationship. Atleast, I feel like I'm better at that than I used to be.

So now i'm the king of the 1-month relationship. ;)
posted by jak68 at 8:09 PM on August 9, 2006

At one time when I was big into online dating, I was dating, to one degree or another, six women at once. I was also looking for a monogamous, future-thinking relationship.

Dating even two women at once was a Bad Idea. Six was nearly disastrous. And in the long run, none of them liked the fact that I had been dating other people at the outset.

Then there was, for me, the worst possible outcome: I decided to see one woman exclusively and broke the news to two others. The relationship didn't last, but I became close friends with one of the other women -- a woman who will not date me because I picked someone else and she will not be second choice. Four years late and I'm still kinda choked that I made the wrong pick. Had I only dated one at a time, I would have inevitably had a steady intimate relationship with the second woman. I missed out on daily blowjobs for the rest of my life because I picked poorly.

So, don't pick poorly.

I recommend dating one at a time and rejecting them before you move onto the next one. Better yet is to avoid talking with more than one at a time; if they're responding to your ad, pull or hide it early.
posted by solid-one-love at 8:10 PM on August 9, 2006 [1 favorite]

Best answer: Shoulda previewed: jak68 makes an excellent point: once you've been online dating for a while, you can sniff out dealbreakers and 'taquito moments' very quickly. Seldom takes me more than two dates. Took three month last time, unfortunately, but that's neither here nor there.
posted by solid-one-love at 8:13 PM on August 9, 2006

a woman who will not date me because I picked someone else and she will not be second choice

seems kinda harsh to me.
posted by Brandon Blatcher at 8:27 PM on August 9, 2006

seems kinda harsh to me.

It's funny; most guys I've talked with about this can't get their heads around the concept, but most women I've talked with about it have considered refusing to be the fallback girl a given.
posted by solid-one-love at 8:31 PM on August 9, 2006 [1 favorite]

Best answer: See previous sort of similar question.
posted by FlamingBore at 8:32 PM on August 9, 2006

Oh, and don't use superlatives.

"Aw, honey; you're the most..." anything is dangerous.
posted by baylink at 8:33 PM on August 9, 2006

a woman who will not date me because I picked someone else and she will not be second choice

I actually picked the wrong guy many months ago, and the other won't date me for the same reason.
posted by echo0720 at 8:48 PM on August 9, 2006

Nice to meet you, jak68 - I'm a stud. ;-)

I've dated multiple women openly and, um, not so openly, and I urge you to heed your fellow mefites calls for HONESTY. It may cost you some opportunities, if some of the women in question are not amenable - but better to lay your cards on the table from the outset.

a woman who will not date me because I picked someone else and she will not be second choice

I dated a wonderful woman once for 4 years, and for all 4 of those years I never stopped hearing about how she liked me for 3 months before I was willing to go out with her. Never mind that we went out for FOUR YEARS, we lived together, we arranged our lives around each other - all that mattered was that it took me three months at the outset to catch on. I didn't string her along or anything - I wasn't dishonest - it just took me awhile to get on board. But once I was on board, I was there. Never understood her grudge, though.
posted by fingers_of_fire at 10:00 PM on August 9, 2006

Am I the only one that thinks Jay is trying to talk himself into this?
posted by Monday at 12:00 AM on August 10, 2006

Best answer: My rule has always been that as long as things stay platonic I can see as many people whose names I can keep straight. (And okay I haven't been able to do that perfectly, but fortunately the guys usually have a sense of humour or at least perspective about it.) I never ask them if they're seeing anyone else - it would never occur to me - and if they ask me I tell them about my rule, which they've always agreed was reasonable.

It's non-problematic, so treat it as such. Don't even think too much about it. Your emotions will sort things out for you and eventually you'll find you only want to be with one person. Or not, which means you should keep looking.
posted by orange swan at 5:26 AM on August 10, 2006 [1 favorite]

Best answer: Don't do it if you don't want to do it. My head can't handle it, and I was always much more comfortable focusing on one person at a time. I was much more comfortable with being the only one focused on at a time, as well, and finding out otherwise lowered my opinion of the man. It's kind of cheesy - where's your gold medallion, you wild and crazy guy?

If you want to try it out, though, here's some don'ts:

-During a date: "Oh, just so you know, I have a date with someone else tomorrow/Friday/later tonight/whatever." Just so you know? Baby, I just wanted you to know how hot I am, in case you couldn't tell already oooh tsssss!

-Overbooking. "Yeah, let's do this again! Friday? Oh, um... No, Saturday's, well... Next Friday is...oh. Hey, I can do lunch a week from Sunday, how's that?"

-After making plans for the next date, immediately updating your online dating profile so it's nice and fresh for all those better options that must be out there.

Do be solid and straightforward and absolutely do not lead anyone on to think that you like them more than in a hanging-out way unless you are ready to stop comparison shopping. I think holding back is a crappy way to start a relationship, but if you're playing the odds and do not want to incite drama that's what you need to do.

It may matter what social pool you're dating in, though. I'm a geek girl and I like straightforwardness and honesty and not having my head messed with, and my geek husband's got the goods. There are some girls who live a more complicated social life, and they like the competition and intrigue. I think their rules may be a lot more complicated, though.
posted by Lyn Never at 6:30 AM on August 10, 2006 [1 favorite]

@ purephase: Maybe not so foolproof, but definitely idiot resistant.
posted by tdreyer1 at 7:38 AM on August 10, 2006

It's funny; most guys I've talked with about this can't get their heads around the concept, but most women I've talked with about it have considered refusing to be the fallback girl a given.

How odd, I don't see it as a the fallback girl, merely as having picked wrong.
posted by Brandon Blatcher at 8:16 AM on August 10, 2006

The relationship didn't last, but I became close friends with one of the other women -- a woman who will not date me because I picked someone else and she will not be second choice. Four years late and I'm still kinda choked that I made the wrong pick.

If this was me, I'd say to her one day: "I need to talk to you. I MADE THE WRONG CHOICE. You're not second best; I just didn't know you then like I know you now. I want to be with you."

Or, you know, words to that effect. But then I have a bit of a tendency to hang myself over cliffs with this declaring-your-feelings kinda stuff, so each to their own I guess.
posted by reklaw at 9:30 AM on August 10, 2006

Response by poster: Thanks all. And solid-one-love, I can't believe you didn't just sign that nick up for this thread. :-)
posted by callmejay at 9:43 AM on August 10, 2006

a woman who will not date me because I picked someone else and she will not be second choice.

That's silly. She doesn't sound so great.
posted by footnote at 11:17 AM on August 10, 2006

I felt the same way when I started online dating. In my case, 90+% of the women would not go on a second date with me. This led me to the conclusion that they were ruthlessly chasing perfection and that I should do the same (other interpretations were unpalatable). Treat people you don't know well as you would strangers; they surely don't deserve exclusivity, and they don't deserve better treatment than they would give you.
posted by jewzilla at 6:33 PM on August 10, 2006

jewzilla: yeah, you're right. I ran into that as well. I ended up going on dates with different people until I met and clicked very well with my current girlfriend. At that point, I cancelled any other dates.

People have been doing this for decades. The internet has just made it more of a pain in the ass.

And OP: when you say "dating" are you actually saying "sleeping with?" You didn't really specify. If you're just going to dinner & a movie, then go for it, it doesn't matter. Chances are the women are doing the same thing anyway.
posted by drstein at 1:34 PM on August 14, 2006

You MUST date more than one woman at a time until you have a commitment that you guys are exclusive. Date as many women as possible. It makes you far less needy.
posted by DanTolumbro at 10:04 PM on November 24, 2006