Posts Tagged ‘dating


setting the ex up with someone new

Reader N.G. writes:

I casually dated a guy for a while, and things didn’t work out. It wasn’t a bad break up and we’re still technically friends, although we don’t hang out alone together or anything — we just spend time in the same social circles. A few weeks ago, I brought a new friend to a party, and she was asking me questions about him. I think she’s kind of interested in him, which is great, because he hasn’t been dating anyone in a long time. I would be totally happy if he started dating a new girl, and I’m not jealous at all, but I don’t know if he’s her type. Still, I think she has a right to figure that out on her own. Of course: she doesn’t know we ever dated. So, should I tell her we dated, or tell her I don’t think he’s her type, or encourage her to try things out with him anyway, or what?

Dear N.G.:

It’s very kind of you to think of the happiness of both your new friends and past exes. It’s also great that you’re capable of moving on, especially since you only casually dated this guy and you still hang out in the same social circles. Good job on keeping things from getting awkward. Hopefully he feels the same way.

I tend to believe total honesty is the best route in all things relationship. However, given the casual nature of your relationship with both of these people, I don’t think it’s necessary to divulge that you dated the guy in question to your new friend.  Unless you know something really damning about him (like, he’s abusive or he has an STD), let her get to know him on her own time. Some relationships should just take their course.Who knows? They may be perfect for each other.

Unify and conquer! Photo by stockimages,

Unify and conquer! Photo by stockimages,

Telling her straight up that 1. you used to date him and 2. you don’t think he’s her type can make you look like a jealous, territorial girl, even if you’re not at all jealous and actually want them to date. If she gets really deep into asking you questions about him, you might mention it for full disclosure, but I would not lead with it. Wait until she’s pretty close to having her own ideas about him before you plant that in her head. The fact that he’s casually dated you may taint her impressions of him, obviously.

On the flip side, I would not go overboard in trying to set them up, either. Pushing her on him could be just as disastrous to the unawkward vibe in your current setting as warning her off him would be, especially if he really isn’t her type. He will probably hear of it and figure it out as well, and it can be somewhat insulting for an ex to set you up with someone new; it could be seen as a “you can’t do this yourself and I need to get you out of my hair” gesture, depending on the guy and your relationship with him.

To sum up: my best advice is to play this cool. Don’t offer more information than necessary; keep the past info to yourself until it’s relevant; ask more questions than you offer details. Let this blossom as organically as you’d let any relationship between acquaintances or casual friends. Save the real matchmaking for your besties.


the half-age plus seven rule

Reader M. A. writes:

A friend of mine who is 40 is dating a girl who is 22. His friends (including myself) are all in our late 30s/early 40s, and while she’s pretty hot and smart, it still icks us out. Are we just a bunch of old fogies being jerks, or is he violating some rule by bringing this girl around?

Dear M.A.:

I’m going to state for the record that yes, you are an old fogey. And you may just be jealous that he can still score hot young chicks and you can’t. (Notice I’m not saying that women in their 30s, 40s, 50s, and 60s can’t be smoking hot, please. ‘Cause I know plenty.)

But you’re also right. He is violating a rule. It’s not necessarily a rule he may know about, and there aren’t any laws about it, but it’s a pretty good rule I think many people follow, even unconsciously, as they decide who to date in life, and how not to be a creep.

So if we’re going to impose rules on our loving, then I guess the half-age plus seven rule is as good a rule to live by as any.

If you are incapable of clicking on that Wikipedia link, I’ll tell you the general premise:

It is acceptable to date anyone younger than you as long as they are no less than half your age plus seven years. On the flipside, it is acceptable for you to date anyone older than you as long as your age is at least half theirs plus seven years.

Make sense?


Yay math! Image:

So your friend is 40. According to our rule, his acceptable dating age range would be (40/2 + 7 =) 27 and older for the youngsters, and (40= x/2 + 7 (solve for x)…) 66 and younger for the older age of the spectrum. (Yes, I did have to pull out a sheet of paper and utilize my seventh grade algebra skills, so thanks, Mrs. Cook!)

Your friend is obviously dating someone who is five years too young for him, according to our rule. And if your friend believed in this rule, then you could ridicule him incessantly for breaking it.

According to this rule, your friend is a creep, and you guys have every right to be icked out by his relationship.

But if there’s one thing we all know we can’t control (maybe), it’s who we fall in love with. You can meet someone who’s practically perfect in every way on paper, and find there are no sparks off the page. And you can meet someone who is just clearly wrong for you and fall head over heels without warning. It’s all chemistry (plus good lighting and probably alcohol, in many cases), and there isn’t much anyone can do about it.

It’s possible he’s just dating this girl because she’s, ya’ know, hot. (The story goes that when Lauren Bacall started dating Humphrey Bogart, she was 19. He was 44. She told her mom, “He likes me! He really likes me!” And her mom said, “You’re 19. What’s not to like?”) In which case, it’ll fizzle out when she gets bored of his taste in music (“What, no Ke$ha?”) and he gets tired of her not getting his jokes. Possibly your teasing will help highlight to him the generational disparity in their tastes, and push the break up right along.

Or it’s possible they’re just one of those odd couples who are going to work out, regardless of generational differences or what the world thinks of them. In this case, you can make fun of your friend mercilessly, but that may just drive him closer to his newfound beloved. They may just start seeing themselves as a team — us against the world!

Like I’ve said before, you can’t tell someone who’s in love that you don’t like their beloved without endangering your friendship, so if he’s really sold on her, you’re just going to have to get used to it. Of course, if you think there’s anything to be concerned about (is he acting differently? dressing younger? not hanging out with his friends as much? doing things you don’t think he enjoys just to keep up with her?), let him know, even if it could mess up your friendship.

If this is just some weird crisis thing he’s going through (after a recent break up with a serious gf, perhaps? or a divorce? or the loss of a parent?), the whole relationship isn’t fair to the young lady, either. When a relationship isn’t right, sometimes we need our friends to pull us back to reality. He could use your help in this situation.

Otherwise, you could be a real pal and just watch as their relationship develops, and possibly get to know her. Maybe you’ll find she’s an old soul. And maybe you’ll get over the ick factor. If it’s meant to be, they’ll be together, whether you, the rules, or anything else likes it or not. And if it’s not meant to be, their relationship will end, possibly in a fireworks show, at which point you can thank them for the entertainment, at least.


pre-empting the friend zone

Reader J. J. writes:

I’ve gone on a few dates with a girl I really like. We’ve been emailing and texting and even talking on the phone a lot since our first date, which I think is a good sign. We’ve even kissed successfully. The other day we were talking over IM and she asked me where I thought the relationship was going. I told her I think she’s great and I want to keep seeing her. In response, she told me she likes me too, but she thinks she could see us becoming friends instead of dating (so I guess it’s not definite?). Does this mean I’m already in the friend zone? Or can I do something to make sure I don’t end up there? We’ve got another date planned this week. Any ideas?

Dear J.J.:

This is definitely a toughie. She’s giving you some mixed signals if she’s saying “friend” while still kissing you goodnight. But I don’t know her motives or her history or anything else about her, so I can’t say for sure what she’s thinking.

Yes, staying out of the friend zone entirely is your best bet for not ending up there. It’s an extremely hard place to get out of, if it’s possible to get out of it at all. But the fact that she’s already said she could see you as a friend worries me that you’re already there.

Here are a few things I think could be going on in her head:

Let's be friends!

Let's be friends! Image: graur razvan ionut /

– She’s afraid of getting hurt, so she’s playing it safe. If she tells you she thinks you could be friends rather than dating, she keeps the upper hand while you’re dating. She could just be telling herself this because she’s been hurt in the past and already expects things to go sour, and if/when they do, if she can convince herself she didn’t want you in the first place, she’ll feel better about it.

– She really does think of you as a friend and just isn’t totally conscious of it. This is the answer I’m leaning towards, just because if she’s capable of saying “I think we’ll be friends”, that’s what she’s thinking somewhere inside. She’s still giving you a chance, which is nice, but it could mean you’re about to get crushed under the weight of “well, I’m really not that attracted to you”.

If the first situation is the case, then you just have to be patient and act oblivious. Keep going with your romantic intentions and don’t stray into friendship territory. If she’s protecting herself, it’s something you’ll have to deal with in the relationship as a whole later on, but at least for now you’re not in the friend zone. Just ignore the “friend” comment and proceed as normal.

If the second situation is the case, you’re basically effed. Unless you want to be friends, of course. The friend zone is like a black hole that you can’t escape from once you’ve reached the event horizon. Even just dipping your toe in it means you’re sucked in and there’s no way back out.

But maybe you can try anyway. Here are a few ideas for your date, either way:

Go romantic.

Eschew anything even remotely “friend-like”. Make clear your intentions are romance, not friendship. Bring her a small bouquet of flowers or a similarly romantic gift (three roses? a box of chocolates? It’s ok to be generic, you’ve got an agenda here and the clearer you can say it through culturally-accepted symbols, the better.) Go out to dinner somewhere and split a bottle of wine. Lean in close and hold her hand. Go in for the kiss. Make sure there’s tongue. NB: I will NEVER advocate forcing yourself on a girl. If she backs away from your advances, let her back away. You’ll know for sure she’s not interested. Never ever do something if she tells you no.

Go sexy.

Make her dinner at your place, and get into a game of strip poker. Or give her an erotic massage. A generic massage is nice, but an erotic massage is a great way to get into the sexy (i.e. NOT FRIENDS) area without necessarily having sex. Again, don’t force it. If she says no or backs off or checks her watch and says she has to go, let her go. And I mean entirely.

Go down in flames.

Take her to a strip club or a sex shop or something along those lines. If she’s put you in the friend zone already, you might as well go out with a bang. She’ll get the hint, probably.

Hopefully you get the romantic response you’re looking for, and she’ll can the “friends” thing, and it’ll be something you can joke about later. Good luck!


a date with a waitress

Reader N.A. writes:

Is it possible to score a date with a waitress? They seem impenetrable, since they’re constantly flirted with (especially a cocktail waitress) all day long.

Dear N.A.:

While I think it’s possible to score a date with a waitress, I don’t necessarily think it’s a good idea to try to score one. Especially cocktail waitresses. And bartenders.

Coffee and dessert

"Yes, I'd love coffee, and dessert, and a date with you." Image: Daniel St.Pierre /

By now you all know how I feel about dating people at work (i.e. DON’T DO IT). The same goes for trying to date people who are working, particularly in the service industry. What I mean is, don’t try and pick someone up while they’re at work, even if you’re not working with them. It’s not fair. It’s a waitress’s job to be nice to you, and to give you stuff you want. Asking her out on a date while she’s working is awkward and could, from some perspectives, be considered sexual harassment, depending on how far you go with it. It’s not like shooting fish in a barrel, although there are several people who seem to think it is.

This is especially true at strip clubs, where sex appears to be on the menu. You have to remember that this is not the case. Strippers are paid to act like they are sexually interested in you. About 98% of the time, they’re not. Do not assume you are a lucky member of the 2%. Your best bet is to let the women do their jobs without harassing them. Would you harass a secretary, or a nurse, or a librarian? (Please tell me no.)

I’m not saying that it’s impossible to pick a girl up when she’s waiting tables or tending bar (or putting away books or answering phones or drawing blood). You’re just setting yourself up for getting into a lot of trouble or making things really terrible for her if you try too hard.

If you do see the girl of your dreams holding the tray before you or standing behind the bar and you can’t stop yourself, here are my tips for your best chance:

Wait until after she’s done being your server. Write your name, number, and a “I think we could hit it off” on a piece of paper (or on your business card) and leave it with the check. Or put up a post on Craigslist missed connections or in your local newspaper’s “I Saw You” section. If you’re feeling very brave, you could try and find her on Facebook and send her a message, but make sure you don’t just send her a random friend request. You don’t want to be a stalker. And do not, for any reason, say something while she’s putting your drinks on the table or taking your order or interacting with you as a server. That’s what makes it awkward.

Don’t over-tip and hope it’ll make her like you. That just screams “I use money to get what I want and I expect it’ll always work”, and no (or at least very few) girls want to feel that they’re the object of your moneyed affections.

Don’t go back to the restaurant or bar over and over, especially if she doesn’t respond. Sure, it’s nice to have regulars. But having a stalker is not cool. If you’ve asked her on a date in her off-time, be very tactful about going back to the restaurant when she’s working. Try not to sit in her section. Be casual about it, and take rejection well, but do not harry her about it or make her feel more uncomfortable than she probably already does.

Remember that if this is your regular joint, you are going to make things extra awkward for everyone if a) she says no, or b) you do date but it doesn’t end well. It’s a thin line to tread. Just be aware that you may have to quit going to your bar for a while if the relationship goes sour, or if she’s really offended that you hit on her. If it’s at a strip club, you could be kicked out or barred from coming back. Choose your battles, amigo.

I will admit fully that it is far easier for a girl to pick up a male bartender or server than it is for a guy to do so with a working woman. It’s not fair, maybe, but it’s just how sexual politics works out. Still, I think women should take this advice to heart just as much as men should, because men can be made uncomfortable by unwanted advances, too.

Finally: You’re right – we girls tend to get hit on all the time, especially when we’re working a casual job like waitress, barista, or bartender where we have to be friendly, sweet, charming, and cute. You are wise to be aware that you’re probably not going to be the first man to proposition her while on the job. And that can totally wreck any chance you could possibly have. But you can be classy about it, and not put her on the spot. Or you can look elsewhere for your romantic endeavors.


the right gift for the new her

Reader Z. N. writes:

You talked about what to get your new mother-in-law for the holidays, but what about a new girlfriend? If you’ve only been dating a few weeks or months, what’s the expected gift from new boyfriend?

Dear Z.N.:

Expectations vary from girl to girl and from relationship to relationship. I don’t know your GF, so I can’t tell you if she’d prefer a book to a pair of earrings or bath salts.

a present!

Image: Francesco Marino /

There are other factors that go into what you get a lady for Christmas or Hanukkah beyond how long you’ve been together. For instance, how serious are you two? I know you said she’s your girlfriend, so I’m assuming you two have had the exclusivity talk at least. If you’ve only been “dating”, and aren’t exclusive, a nice card and a flower or special candy or something is probably fine. If you’ve only been hooking up, I don’t even know if I’d advise giving her that much. It depends on how much further you want the relationship to go. Giving someone a gift or card at the holidays means, “I care about you and want to continue getting to know you better.” Giving something to a hook-up could give a signal that you’re interested in more, so be careful with that.

Furthermore, if you guys were friends for a long time before you started dating, you might be more serious with each other than a girl you’ve just met. You probably also know a lot more about her, and buying a present should be that much easier for you.

While I can’t say for certain what your lady friend would like or what’s totally appropriate, I do have a few tips to steer you clear of asshole boyfriend territory:

Get her something. Anything.

I could say that if you’ve only been dating for a few weeks, she probably isn’t expecting anything for the holidays. But that would be a lie. Even if a girl says she doesn’t expect you to get her something for the holidays, and even if you’ve only been dating for a day, GET HER SOMETHING FOR THE HOLIDAYS. I don’t care if it’s a single rose from the gas station down the street or a box of wine, you give her SOMETHING. Same goes for birthdays. Otherwise, you’re that asshole boyfriend who couldn’t be bothered to get creative. Trust me on this one.

Don’t get her something you want.

Apparently guys do this all the time. It’s probably something you won’t have to worry about until later on in the relationship (i.e. when you’re actually living together), but it’s something you should check yourself for anyway. My major advice here: Avoid electronic equipment unless she has specifically asked for it. A pair of nice headphones? Okay, not a bad idea, especially if she’s been complaining that her earbuds are busted. A new Wii controller because you play Wii a lot at her place? Mehhhhh that’s not very personal. Even if you play Wii together, that could be seen as veering more into “I’m a guy and I will use this” territory. The reason we give gifts is to show people that we’re thinking of them, not of ourselves. Keep that in mind.

Don’t spend too much.

If you give her diamond earrings after your first two weeks together, you’re setting the bar pretty high. Diamonds after two weeks? What happens at your first anniversary? A house? If you can find her something nice for under $50, go for it. I’d say $25 is almost steep if you’ve only been together two weeks. There are lots of inexpensive gifts out there. Don’t blow your load early — save a little something for a few months down the road. Expensive gifts are typically gifts that are supposed to last, and should be saved for relationships that have lasted and/or will last.

Show off your knowledge of her.

This is your chance to prove to her that you’ve been listening. Even after two weeks of being with her, you should know at least some of the things she likes (and dislikes). Don’t go out on a limb with something you’re not sure she’ll enjoy. Play it safe. Even if it’s just something small like a bottle of wine or a gift certificate to a place she’s said she likes, you’re sure to win if you show that you know what she likes. It’s probably too early to know her taste in jewelry, too, so unless you’re sure you know her inside and out, I’d advise you to watch out in that arena. Food or a gift certificate are probably your best bets here, too. (And no, I don’t think a gift certificate is a bad idea for a new relationship, as long as you get it for something or somewhere she really likes. Just don’t play this card after you’ve been together longer than two months.)

And my number one advice for you: Don’t stress out about it. Remember that it’s the thought that counts, and a little can go a long way.


getting him to make the move

Reader T. M. writes:

I’ve been hanging out with a guy I like for a while and I think he likes me, but he won’t make a move. How can I get him to ask me out on an actual date or something?

Dear T.M.:

I think you have three options:

1. Wait forever.

2. Make the move yourself.

3. Move on to a guy who’s more aggressive.

In my experience, if a guy doesn’t make a move, it’s either because he’s too shy or he’s not interested. There’s a slight possibility he has no idea you’re interested, which is basically exactly like being too shy.

So what I’m thinking will happen is: nothing. Unless you make a move.

bigger man

Go on, be the bigger man. Image: graur codrin /

While I am personally a greater fan of the guy making the first move (just like you, apparently), we actually live in an era where it’s always Sadie Hawkins time. Being slightly aggressive is no longer shunned or relegated to hussies and hos. Sack up them ovaries, tell him how you feel, and ask him if he feels the same way. Remember, rejection is good for you.

You can be coy about it and ask him why he hasn’t ever asked you on a date. Or you can be a real girl and straight up ask him to dinner, and make your intentions clear. Say to him, “I would like to date you. Are you interested?” He may be taken aback (particularly if he’s shy), but at least you’ll know whether he wants to date you or not.

You can try flirting harder, and giving him even broader hints that you want him to be romantic with you. Maybe he’s completely oblivious to your intentions. Guys can be strangely thick sometimes, especially if they lack a bit of confidence. But usually I find people who are oblivious are there because they want to be, and not because the other party isn’t being totally clear. He may not be attracted to you, and he may want your friendship to stay the way it is, and he may therefore be oblivious to your advances. This is why direct questioning is the best way to go. Get it out of the way.

You could also get a friend to tell him to ask you out. Then if there is rejection, it comes at you sideways (from your friend) rather than head-on (from his mouth). It’d be rather passive aggressive of you. It’d also be very seventh grade of you. And who didn’t love seventh grade? (That would be me; I hated seventh grade. Hence this option makes me roll my eyes. It’ll work, but it’s stupid.) (And maybe, technically, if he reads this blog, you’re basically doing the “have a friend tell him” thing through me. Damn, I’ve been caught in your web!)

Of course, moving on is probably my favorite option. If you’re not getting what you want, find someone else who will give it to you. We ladies always forget that you don’t have to be tied to anyone, especially not someone you’re not married to. You’re not even dating this guy yet. There are very likely some really nice crushable guys around you that will actually ask you out without needing to be instructed how. Find one of them and flirt away. If your current boy is actually interested, he may take up the competition and ask you out of his own volition. Or he may sneak away into the woodwork, in which case he’s not your type anyway.

The fact is, if you want a guy who will ask you out, this may not be the guy for you and you’re going to have to admit that. If you like this guy for who he is and want to date him, the ball is in your court.



Reader D. E. asks:

What does “exclusive” mean in terms of a relationship? What I mean is, the guy I’m seeing wants to be “exclusive”. I said OK. Do we need to discuss this further? Are there rules of exclusivity I should be aware of before I really commit to this?

Dear D. E.:

I think this is one of those play-it-by-ear situations. “Exclusivity” means various things to various people. The most basic definition I can come up with is “not sleeping with or dating other people”. You’re going to have to ask your partner to give you details. Does it mean you’re completely monogamous and therefore not using condoms anymore? (Probably.) Does it mean you have to shut down all your online dating sites and not accept dinner invitations from other men who are seeking your attentions? (Probably.) I wish I could tell you a more definitive answer, but you know your man better than I do.

old people

I think these two are exclusive. Image: Arvind Balaraman /

However, “exclusive” does not necessarily mean this fellow is officially your boyfriend. I wouldn’t start inviting him to family holiday functions or expecting long weekends away just yet. “Let’s be exclusive” is a far cry from “let’s get married!”, or even from “be my girlfriend”.

Of course, if he’s the one asking for exclusivity, he probably does want to be your boyfriend. Rarely have I come across a fellow who was willing to ask a girl to be exclusive who was not also willing to ask the girl to be his girlfriend, but you never know. You’re going to have to ask him about it, if you really want to know.

But for the time being, how about you define it for yourself?

In my personal experience, I find that I cave into demands from partners far more easily than I probably should. (Hindsight is always 20/20.) Do you want him to be your boyfriend? Do you want to quit seeing other people? Are you ready for that? Decide on the rules that you need and lay them out for him. Be honest. If you aren’t ready to give up those titillating dates with other men, your new partner in exclusivity needs to know it now rather than in three months when you explode in a cheating rampage of doom.

I think that we ladies get caught up in the romance of being wanted and forget what we actually want sometimes. If you’re not ready for “exclusivity”, don’t pretend you are.

But if you are ready, and know what you want and are prepared to get it, well then… mazel tov!

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