How do you approach a total stranger and hit on them?

OK. I have been divorced since Feb and am starting to feel like I am ready to go out and try to date some people. The problem is that I am pretty shy around women. I know I am not an unattractive man, but I look VERY young for my age. I am 25 and look like I am 18. I am not exaggerating. It makes it tough for me to approach women who are my own age because I feel they are looking at me like I am a child.

The other problem I have is that women from the age of 18-28, all look the same. I am having a VERY hard time telling if the women I find attractive are even old enough to drink. I don’t really want to get involved with a young party chick. Those days are behind me.

The third problem is that I am terrified of rejection. I have never actually asked a girl out in my whole life. They have come to me. So I really puss out in the clutch.

All of “our friends” became “her friends” after the divorce so I don’t really have a social life as it is. I don’t have a group of guys that I can go scope babes with. So the situations I am talking about are the women I just see in public and think are hot.


Getting my hair chopped at Supercuts. Hot chick working the counter. Can’t tell how old she is. Could be 25, could be 17. Who knows. Anyway, how do I approach her with the intent of getting her # without a line that sounds like a pick up line? Why would she talk to me? Kinda like whats his ass said in Office Space when his friends told him to go talk to Jennifer Aniston. He says “I can’t just ASK her out. I am just another asshole customer to her.” How true that statement rings.
How does a gay guy, or lesbian, hit on a person whom they don’t know whether or not is gay? There must be some special technique for that kind of circumstance. I think that type of tactic is what I need. Covert Ops. Try to pick her up, but she doesnt know it, so if she says know I can tell myself that I didn’t get rejected.

Sound do-able? Hope so.

BTW. I hope I didn’t offend anyone with the gay guy, lesbian thing. I jsut figure that you guys are dealing with a really big unknown there when asking out someone you aren’t sure about. I want to use the same tactics.

Best way is to spend alot of time striking up conversations with people you are not interested in having sex with. People who only come out of thier shell when talking to someone they want to have sex with are very obvious: they are awkward, uncomfortable, and their eyes keep drifting. There is clearly a “goal” for the conversation, and the presense of a goal translates into feeling pressured: the person being hit on gets the distinct impression that ithe person is 1) looking to hook up and 2) if they fail to hook up, will think that they were “wasting their time”, which is not flattering.

On the other hand, genuinely friendly people who talk to anyone are comfortable, and thier conversations are open-ended. Plus talking to anyone will give you experience ocming up with things to talk about.

That said, striking up random conversations is not the best way to meet people, though it is how I met my husband. The best way to meet people are when you have repeated contact with them in a social setting, as that allows you to build trust and raport over time, not in a 10-min stretch. You need to get out–go back to school and take a totally useless class in something you love, go take dance lessons, join a biking club, join your church’s single’s group if you are religious, start donating blood as often as they willl let you. And don’t walk away from a group if on the first day there isn’t anyone you want to bang: all those people have sister, cousins, roomates, and coworkers.

And always, always, always remember that being too goal-oriented here sends off the worst vibes in the world. If the only reason you are doing something is to find love/sex, go do something else. And if there is nothing you enjoy doing with other people and the only reason you are willing to leave the house is to hook up with a potential partner and you can’t help but think that if you don’t hook up with a partner any activity will have been a waste of time, then you have a tough road ahead of you, becasue it is very diffucult to meet someone to love if you don’t even like spending time with other people.

" Getting my hair chopped at Supercuts. Hot chick working the counter. Can’t tell how old she is. Could be 25, could be 17. Who knows. Anyway, how do I approach her with the intent of getting her # without a line that sounds like a pick up line? "

Ask her for the business card for the store, presto, you got her work number.

Well, first of all, don’t let on that your nickname is “Stinkpalm”!

That could be creepy, Handy. Calling someone at work unsolicited probably wouldn’t go over well.

I kind of like MandaJo’s advice but I have no problem chatting the person up after only meeting them once or twice (if time permits).

How did you meet you ex?

Well, usually, if a guy is in a gay bar, or in a gay chat room, or at the pride parade, and he’s not gay, he’s usually cool enough to say, “Thanks, but I’m not gay” without pitching a fuss.

An eagle eye can also spot telltale signs like an excess of rainbows or a certain insecurity about gender pronouns.

Failing that, there is gaydar.

Anyway, to your question: how to hit on a stranger? I recommend starting up a conversation, finding a topic of interest, and pursuing it for a little while, and then inviting the object of your affections to continue the conversation over sophisticated adult beverages. Works for me.

Sometimes you can go risky, and may have it pay off. I once had a guy come up to me on the street, tell me (I’ll quote): “I noticed you buying CDs, and I thought you were really beautiful. If you don’t have a husband or a boyfriend I’d really like to take you out sometime.” Occasionally, a little unsolicited flattery from someone can get you everywhere. I gave him my phone number, and we did manage to go out several times and kept in touch for a few years. Nothing serious came out of it, but I thought it was a pretty ballsy approach for meeting a complete stranger, who turned to be a totally decent guy and a fun date.

Try “Hey, my dick isn’t gonna suck itself, so you wanna get out of hear?”. Someone reccomended it to me in a thread about the polite way to ask for oral sex. He was joking I think, but it has worked real well for me.

I get a laugh, and a playful smack. Then I say “Isn’t that funny? But seriously. Suck my dick.”

Maybe I’m not the best person to ask.

DaLovin’ Dj

From an e-mail I sent to my singles buds a while back:

Substitute “dance with you”, chat with you", “have coffee with you”, or whatever for “get horizontal”, unless that is the goal.


I’ll go along with the suggestions given so far, but it’s also sounding like you’re feeling very shy about all this.

Try online personals.

You still get rejected, but for me at least it’s a lot easier to handle the rejection. This person has only gotten to know “me” through pictures and the typed word, so it feels like less of a rejection of me and more of a rejection of my technique.

I’ve also found that the introspection necessary to come up with what is important to you and what you are really looking for is helpful in off line dating situations as well.

Add to that you don’t have to worry about whether they are looking or not, they are posting a personals listing, so they are looking.


Stinkpalm, read Manda JO’s advice several times. It is good stuff.

The only thing I would add is to try to change your view on rejection. Flirting with a cute girl you don’t know, even if you don’t end up asking them out, is a very brave thing to do. It is, in itself, worthy of respect, regardless of whether or not it goes anywhere. Take pride in your bravery and the fact that you’re out there taking action, and not just sitting back and being lonely. It really changes the whole dynamic.

During my last single period, I got very pro-active and started flirting with and asking out women. Once I focused on the pride of doing something both foolish and scary, it was great fun. Women love to be asked out, if you do it nicely. It’s a compliment. And I dated a few people because of it. It’s worth taking risks, as long as you don’t take rejection personally. If you project confidence, you’ll be a hundred times more attractive to women than if you don’t.

That all said, getting to know people first is generally easier and leads to longer-term relationships, in my experience. But flirting with strangers can be a lot of fun, and worth a try.

Stinkpal, you have nothing to loose and a lot to gain. I mean your alone right know if you try and fail you will be no worst. So go for the hot chick.

You could do what I did after I split with my ex: Sleep with the women you work with until that old self confidence builds back up.

Ok, maybe not.

Here’s a better idea. Make friends first. Don’t worry about getting laid, that’ll come later. As you rebuild your social life, you’ll be introduced to new people as your network of friends (and moral support - you need it!) grows. You’ll be casually introduced to lots of new girls along the way. Don’t think you have to hit on every little pretty thing you see.

And stop worrying about their age! If they look too young to you, they are. If you think you’re interested, then what’s the problem? Trust me, if you’re too old (25? please!) they’ll let you know.

And last of all, (and this was something I had a lot of trouble with) learn how to be alone. I know that sounds contradictory, but IMHO you need to be comfortable not having anyone there. You’re used to having somebody with you. It made me clingy as hell & tended to not be very attractive. Once I got past that hurdle my self-esteem rose to a respectable level.

So, recap:

  1. Work on building social life.
  2. Be a recluse.

Just kidding. Seriously though, I hope I’m making at least a little sense here.

And good luck in your new role as “Ladykillin Studman”! You’ll need it with a name like “Stinkpalm”! :smiley:

I like Manda Jo’s advice best.

That said, women have it so much easier than men. I met my husband (El Hubbo) at a bar. He was sitting in a booth, across from someone I knew, so I sat down next to him and talked to my friend for a minute. I thought El Hubbo was cute, I’d had a few beers, so I made a joke about him looking tense and began massaging his shoulders… We had our first date about a week later. Once we were officially “an item,” he admitted that he thought I was a slut when we first met. I thought he was a jerk because he didn’t reciprocate.

Women can be overt with their advances and 9 times out of 10, the guy will (at least) enjoy the attention. Just the opposite seems to be true for men. Sorry guys!

"Try online personals. "


I’m a few years older & in the same boat, my friend. My wife & I split up in March. I have been doing something like Manda JO suggested, talking to all the women at work, whether I’m attracted to them or not, whether they’re 18 or 50. I have started a few friendships out of it & I hung out all day with a little hottie from the office yesterday. The attention really feels good, but I know I’m in no condition to start a “relationship” right now. I figure maybe in a year or so (I’m not exaggerating), if I’m interested in it then I might be ready to start a relationship, but what I need right now is just some attention & company.

As soon as I get the sex thing figured out again (I’m way too fragile for that, If I got nekkid with Miss office hottie right now I’d get all clingy & we wouldn’t be friends for long), I’ll let ya know what I’ve tried & how it’s worked.

I don’t have much to add except on one front: looking young. I have a babyface too. If I don’t wear my glasses, I get carded for beer (I’m 30).

So I got some of those thick-framed, clunky, Buddy-Holly-type glasses to give my appearance a little force and definition, and I found–the very first day I wore them–that people responded to me differently. Maybe it was the glasses, maybe it was a change in my own perception of myself, but one way or the other, there was a difference. Bums stopped hitting me up for change (I was living in a very rough neighborhood at the time). Women began starting conversations with me. Waiters began calling me “sir.”

So I don’t know if you wear glasses, but if you do, that’s something you might try. I was really amazed at the difference.