1. Send a “wink” on Match.com
2. Give her a digital bouquet of flowers as a gift on Facebook.
3. ReTweet him to all your followers.
4. Send a short, simple message to their dating site email such as “Hi!”
5. Tell them their profile picture looks like a specific famous celebrity.
6. Send a Direct Message on Twitter.
7. Give him a compliment like, “Your profile answers are so hilarious!”
8. Ask her what her favorite movie is (…and surprise, surprise, it’s your favorite too!)
9. Buy a Groupon for her favorite type of food and ask her to go to the restaurant with you.
10. Send him an cutesy e-card to his email account.
11. Make a comment under one of her blog posts you enjoyed telling her so.
12. Attach a rose to your message on Cupid.com to show interest.
13. Tweet directly @ him to say hi!
14. Send her a funny face made out of various letter/symbols.
15. Ask her what her favorite Bible verse is on ChristianMingle.com.
16. Change your profile picture to one of you winking – you’ll be flirting with everyone!
17. End your message with a smiley face emoticon.
18. Suggest a fun outing for the two of you on HowAboutWe.com!
19. Write something funny and casual on her wall on Facebook.
20. Send him a digital gift card that he can use for online shopping.
21. Repin one of her pins onto your boards.
22. Point her to a GIF you love of cute animals being, well, cute!
23. Send her a Vine video of you introducing yourself!
24. Ask her to connect with you on LinkedIn.
25. Initiate an instant message conversation.
26. Use a flirting website like www.SendFlirt.com.
27. Tell him you two went to the same college and strike up a convo over your similarities.
28. Have one of your common Facebook friends make an introduction for you.
29. If she’s a movie buff, send her a year’s subscription to Netflix.
30. Send him a SnapChat of you looking flirty (but not overtly sexy!)
31. Favorite one of her Tweets.
32. Ask her a question to start the conversation such as, “What’s your dream vacation?”
33. Take a new profile pic with better, more open body language.
34. “Like” his Facebook status update when it’s about something positive.
35. Send a free smile on a dating site that offers the option, like Unona.com
36. Post a YouTube video of you singing her a song and send her the link.
37. Tell him a joke!
38. Use Facebook’s instant messaging function to tell her you like her profile pic.
39. Share a picture of yourself holding out a bouquet of flowers with her!
40. Send your crush an “ice breaker” question as prompted by your dating site!
41. On Valentine’s Day, send an e-card asking them to be your Valentine!
42. Comment on his Flickr photos to tell him he’s a great photographer.
43. Once you start a conversation, give them a playful nickname.
44. Some dating sites allow you to send “flirts.” Use this function!
45. Send her an message just to tell her you hope she has a great day.
46. Coyly ask, “Hey, don’t I know you somewhere?”
47. “Accidentally” message them pretending to be trying to reach someone else.
48. “Poke” her on Facebook! (But only if she has a sense of humor!)
49. Read their profile to see what TV show is their favorite. Watch the show, then chat them up about it!
50. Give him your number before he asks, “Just in case!”
51. Tell her she’s a great player within a MMORPG like World of Warcraft.
52. Ask her if she’d like to Skype with you.
53. Send her a digital gift of airplane tickets on WhatsYourPrice.com if you’re willing to pay for her to travel to meet you.
54. If it’s her birthday, send her a Happy Birthday message or Facebook wall post!
55. Directly ask her if she’d like to go out! Directness is always admirable.
56. Ask if he has a great recipe to share for that favorite dish he mentioned on his profile.
57. Give her a compliment!
58. Add someone to your Hotlist on dating sites that offer the function.
59. Flirt with her using your Avatar’s body language in a virtual world like SecondLife.com.
60. Give him a digital hug!
61. Invite her to play a game with you on Facebook.
62. Purposely remove your “anonymous searching” setting so your crush can see you looking at their profile!
63. Check out a dating site designed just for flirting like www.FlirtOMatic.com.
64. Send her a picture of you and ask her advice on the outfit you have on.
65. Give her a virtual box of chocolates on Zoosk.com.
66. Mention that you’re taking a trip to their favorite city and ask for recommendations!
67. On a pet-lovers dating site, tell him his dog is adorable.
68. Use a super-cheesy pickup line to introduce yourself if you think she’s got a sense of humor.
69. Friend request him!
70. Endorse her for a particular skill on LinkedIn that you know you can chat about later.
71. Put a link to her blog in your next blog post and make sure she sees it.
72. Ask him in a chat room you’re both in if he’d like to directly message with you.
73. Send her a prepaid phone card with your number on it and ask her to call you!
74. Inquire about their screen name.
75. If she speaks a different language, send her a “Hello! Your picture is beautiful!” message in that language.
76. Check out the Meet Up Groups website for your town and chat up one of the meeting organizers.
77. Remark on what she’s wearing in her profile pic.
78. Post a “Missed Connections” ad on Craigslist in your town.
79. Upvote one of his clever comments on Reddit.
80. Rate their picture as “hot” on a site like HotorNot.com.
81. Send him a digital kiss.
82. Make someone a “favorite” of yours on the dating site you’re both on.
83. Send her a private message to wish her a Happy Birthday and ask about her plans.
84. Find someone whose style you like on Etsy and compliment their wares!
85. Give them a fiverr.
86. Photoshop a pic of them living it up with a celebrity.
88. If you live in the same city, checkin to a place where they are the Foursquare mayor – better yet, steal the mayorship!
89. Repin her favorite dish on Pinterest.
90. Ask him what you’re doing wrong in Call of Duty.