Asking her out for the first date

My friend is freakin’ out about how to ask a girl he likes on a date. He’s 36 and not exactly a novice to dating, but he’s still getting butterflies every time, and feels as though he’s getting nowhere.

I gave him a couple of tips, but I said I’d have more later – your comments of course – if he was willing to wait.

Here are mine…

Be straightforward, and not wishy-washy.

This irks me the most. It’s when a guy will hint that he wants your number, or he’ll faintly suggest going out to a lunch or a coffee after, but he won’t directly ask you. The worst is when you already know each other (not complete strangers) and you’re already friends, which increases the vagueness of anything you ask.

Wishy-Washy
“Hey, wanna grab a coffee?”

If this came from a complete stranger I only just met, I’d know it’s a kind of pre-testing to see if after coffee, how interested they are in you to blow some money on a meal afterwards.

But if it came from a friend, or someone I already knew in the office, I’d assume they are just offering to go to coffee just to be co-worker friendly. Maybe not everyone thinks this way, and maybe the guy is mis-interpreting it and sees it as an actual DATE, but to me, we’re just co-workers going for a beer after or something. The only way to salvage this, is to pay for the night, so she at least gets a jolt thinking: “Hey… maybe this isn’t just as friends. I mean he paid for everything.”

OR

Ask her out on a proper dinner date after the coffee.

Straightforward
“I really want to get to know you better, and not just as co-workers or friends. Do you want to grab a coffee after work?”

This is clear, straightforward and she is 100% clear of on your intention to go out for this coffee not as friends or as co-workers, but as a potential love interest.

Sure, it raises the bar for a louder rejection, but at least you won’t be wondering whether she said yes because she just wanted to be a friendly co-worker, or yes because she’s interested in you too.

If you are interested in her, don’t reveal everything

If you have some crazy-ass issues going on in your life, like your last serious fiancee ran off with your brother, and got pregnant with your cousin’s baby… don’t bring it up. You can bring up this stuff later, but for the beginning, keep your cool, keep your “Hey, I’m approachable and not on the rebound” game face on, and you won’t scare her off.

For me, I had guys in the past who kept talking about some drama they had in their life, and I was immediately turned off from even considering them as a potential love interest because I immediately flagged them as “Trouble“.

There aren’t many women out there who will willingly take on a new guy who is clearly distraught, with many love problems, and is not stable in his emotions and his heart (as in, he hasn’t gotten over the issues) and be okay with dealing with this all the time. What she wants to do, is focus on (HER + YOU), not (YOU + COUSIN + EX-FIANCEE + BROTHER).

Don’t ask women out while on the rebound

..that segues into this tip. If you’re on the rebound and you still have issues going on in your life that you haven’t sorted out, you need to take some time to chillax (= chill + relax, the bastardization of the two English words), and breathe.

Don’t get me wrong. You can ask women out while on the rebound, but ONLY if you don’t want it to go anywhere beyond the physical. But if you’re really interested in her and really interested in the long-term aspect of things, don’t immediately jump into the next relationship…. it won’t be good for you, and you might end up alienating and losing her in the end.

Look presentable and dress for your body

This is for if you see her in the office OR if you are just in Starbucks, secretly checking her out…

I can tell you straight up that guys with a bit of a beer belly, do NOT look good in very thin ribbed knits. It fits all wrong on their body, and if it’s tight – all the worse.

It’s not the body you have, it’s how you dress it and it applies to women and men.

Guys, if you sport a bit of a beer belly, wear structured, pressed, ironed, oxford shirts. They look the best on you because they’ll skim over your flaws instead of hugging them, and they make you look a bit sharper instead of sloppy.

I know some sites may tell you:

Approach the girl you like. Try to dress fairly decent, but don’t overdo it. For example, if you’re a T-shirt and jeans person, wear that. Do not show up with button-ups and ties, because you want her to like you for you, and you don’t want to give her any false ideas. If you have a million stains and wrinkles don’t worry. If she doesn’t like you because of what you wear, she’s not right for you.

But buddy, if you show up to work (every day) or show up on the date wearing an outfit that has a million stains or a million wrinkles or a million holes, you are not going to get a second chance to make a first, good impression.

I cannot imagine any women out there who (on the first date with a stranger, or even a co-worker) will forgive a million stains, rips and wrinkles when you’re showing up to take HER out on a date to gauge the love potential. Imagine if she was also wearing jeans and a t-shirt, but looked a thousand times better than you because she cared about how she looked?

If you care about how you look, it means you care about how you look… TO HER. And that is always a positive thing (like paying for the first date )

Besides, how hard is it to wash, clean and iron a pair of jeans and a t-shirt?

But keep in mind, there may be women out there who will totally write you off for folding your pizza in half, but they’re really the ones who are not right for you, to be nitpicking over something so trivial.

Gauge her interest

This one is tricky because if you work with a lot of people all the time, you don’t want to come off as too standoffish (as a woman) because you want them to not treat you like a robot employee, but as a person. The issue is crossing the line, and how friendly you can or cannot be, before they start interpreting those signals as wrong. I have no real answer on this, every woman is different.. some may think being friendly is not flirting, but some guys will interpret it as such, and others may think that being remotely interested in their colleagues’ life or smiling is flirting, but guys will interpret it as her just being friendly…

I have no clue on this one. It depends. I hate to give such a vague answer, but it does.

And once you’ve sealed the deal, I said:……..

Always pay for the first date

66% of women say that the guy should pay on the first date, while only 60% of guys think so. Sure, that 6% difference is small, but… why take the chance?

I’m a traditionalist in this particular aspect, and like I’ve said before in earlier posts, paying for the first date is a sign that you are interested in her. If she’s interested as well and there are second and third dates, there’ll be plenty of other times for her to foot the bill.

Repeat after me:

The most important date is the first one.

The most important date is the first one.

The most important date is the first one.

So don’t pick a ridiculously expensive restaurant you cannot afford for the first date!! Go for a coffee, but pay for it entirely. She may be able to afford the most expensive restaurant in town, but that’s no reason to have her pay for the first date especially if you asked her out.

And don’t go overboard with the romantic gestures either. She’ll be gagging in the corner while you’re in the washroom, completely uncomfortable and antsy.

So, any other tips for my nervous, sweaty guy friend?

Related Posts:

• Paying for the first date
• Why don’t you return my calls! (For the guys)
• Paying more than your fair share
• Sex and the City 2 – The Trailer
• The Dating Age Gap

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